Alkyl 2-methyl-3-phenyloxirane-2-carboxylate [All Preps (61); 2016-02-16]

Query Query

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Date

61 reactions in Reaxys

2016-02-16 06h:11m:59s (EST)

ALK O O

1. Query O

Search as: Product, As drawn, No salts, No mixtures

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1/18

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O

O

O

O

E

O

rel-configuration

Rx-ID: 39189915 View in Reaxys 1/61 Yield

Conditions & References

69 %

With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetic acid, acetonitrile, Time= 2h, T= 0 °C , enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

O

O

E

O

rel-configuration

Rx-ID: 39190053 View in Reaxys 2/61 Yield

Conditions & References

58 %

With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetic acid, acetonitrile, Time= 2h, T= 0 °C , Temperature, enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O E

O

O O O rel-configuration

Rx-ID: 39190052 View in Reaxys 3/61 Yield

Conditions & References

49 %

With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetic acid, acetonitrile, Time= 2h, T= 0 °C , enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O E

O

O O O rel-configuration

Rx-ID: 39189916 View in Reaxys 4/61 Yield 43 %

Conditions & References With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetic acid, acetonitrile, Time= 2h, T= 0 °C , enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

2/18

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View in Reaxys

H

O

O

O Cl

O

O

O

Rx-ID: 597813 View in Reaxys 5/61 Yield

Conditions & References

80 %

With N-benzyl-N,N,N-triethylammonium chloride, potassium carbonate in N,N-dimethyl-formamide, 1.) 20 deg C, 72 h, 2.) 40 deg C, 24 h Gladiani, S.; Soccolili, F.; Synthetic Communications; vol. 12; nb. 5; (1982); p. 355 - 360 View in Reaxys With ethanol, sodium ethanolate Patent; Knoll A. G.; DE702007; (1938); View in Reaxys With sodium methylate in methanol, toluene, T= 0 - 20 °C , Darzens condensation Zimbron, Jeremy Malcolm; Seeger-Weibel, Manuela; Hirt, Hans; Gallou, Fabrice; Synthesis; nb. 8; (2008); p. 1221 - 1226 View in Reaxys

H

O

O

O

Cl

O

O O

Rx-ID: 2690285 View in Reaxys 6/61 Yield

Conditions & References With sodium ethanolate in benzene, Time= 5h, T= 60 - 65 °C Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953 View in Reaxys Stage 1: With potassium hexamethylsilazane in tetrahydrofuran, toluene, Time= 0.166667h, T= -78 °C Stage 2: in tetrahydrofuran, toluene, T= -78 - 20 °C Concellon, Jose M.; Bernad, Pablo L.; Rodriguez-Solla, Humberto; Diaz, Pamela; Advanced Synthesis and Catalysis; vol. 351; nb. 13; (2009); p. 2178 - 2184 View in Reaxys

N

O O N O

O– Na +

O

O

O O

Rx-ID: 10532185 View in Reaxys 7/61 Yield 87 %

Conditions & References in ethanol, Time= 12h, T= 20 °C Chen, Zhihua; Morimoto, Hiroyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu; Synlett; nb. 20; (2006); p. 3529 3532 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

3/18

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O

O

O

O OH

O

O

Rx-ID: 19141216 View in Reaxys 8/61 Yield

Conditions & References Reaction Steps: 3 1: K2CO3 / methanol / 3 h / Ambient temperature 2: pyridine / 1.) overnight; 2.) 0 deg C, 1 h 3: NaH in mineral oil / diethyl ether With pyridine, sodium hydride, potassium carbonate in methanol, diethyl ether Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p. 8161 View in Reaxys Reaction Steps: 3 1: K2CO3 / methanol / 3 h / Ambient temperature 2: pyridine / 1.) overnight; 2.) 0 deg C, 1 h 3: NaH in mineral oil / diethyl ether With pyridine, sodium hydride, potassium carbonate in methanol, diethyl ether Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p. 8161 View in Reaxys

O

O

E

O

O

O racemate

Rx-ID: 2068122 View in Reaxys 9/61 Yield

Conditions & References

80 %

With 3-chloro-benzenecarboperoxoic acid in dichloromethane, Heating Ayi, A. I.; Remli, M.; Condom, R.; Guedj, R.; Journal of Fluorine Chemistry; vol. 17; (1981); p. 565 - 580 View in Reaxys O O

S O

O

O

O

O

HO

O racemate

Rx-ID: 3604115 View in Reaxys 10/61 Yield

Conditions & References With sodium hydride in diethyl ether, Yield given Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p. 8161 View in Reaxys O O

S O

O

O

O

O

HO

O racemate

Rx-ID: 3604116 View in Reaxys 11/61 Yield

Conditions & References With sodium hydride in diethyl ether, Yield given Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p. 8161

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

4/18

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View in Reaxys

HO O

O

O

O HO racemate

O

Rx-ID: 19123114 View in Reaxys 12/61 Yield

Conditions & References Reaction Steps: 2 1: pyridine / 1.) overnight; 2.) 0 deg C, 1 h 2: NaH in mineral oil / diethyl ether With pyridine, sodium hydride in diethyl ether Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p. 8161 View in Reaxys

HO O

O

O

O HO racemate

O

Rx-ID: 19123115 View in Reaxys 13/61 Yield

Conditions & References Reaction Steps: 2 1: pyridine / 1.) overnight; 2.) 0 deg C, 1 h 2: NaH in mineral oil / diethyl ether With pyridine, sodium hydride in diethyl ether Heathcock,C.H.; Pirrung,M.C.; Young,S.D.; Journal of the American Chemical Society; vol. 106; (1984); p. 8161 View in Reaxys

O O trans trans O trans trans

O O

trans transtrans O O trans O

(+)-enantiomer

(-)-enantiomer

Rx-ID: 28665239 View in Reaxys 14/61 Yield

Conditions & References With 4,5-di-O-acetyl-1,2-O-isopropylidene-D-erythrohexos-2,3-diulo-2,6-pyranose, Oxonereg;, tetra(n-butyl)ammonium hydrogensulfate, (ethylenedinitrilo)tetraacetic acid disodium salt, sodium hydrogencarbonate in water, acetonitrile, Time= 24h, T= 0 - 20 °C , pH= 7.0, optical yield given as percent ee Wang, Bin; Wu, Xin-Yan; Wong, O. Andrea; Nettles, Brian; Zhao, Mei-Xin; Chen, Dajun; Shi, Yian; Journal of Organic Chemistry; vol. 74; nb. 10; (2009); p. 3986 - 3989 View in Reaxys

O O

E

O

O

O racemate

Rx-ID: 348677 View in Reaxys 15/61 Yield

Conditions & References With meta-chloroperoxybenzoic acid, ethyl acetate MacPeek et al.; Journal of the American Chemical Society; vol. 81; (1959); p. 680,683 View in Reaxys With dichloromethane, 3-chloro-benzenecarboperoxoic acid

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5/18

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Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511 View in Reaxys

O Cl

H O

O

O

O O

Rx-ID: 2679262 View in Reaxys 16/61 Yield

Conditions & References

72 %

With potassium tert-butylate in tert-butyl alcohol, Time= 3h, Ambient temperature Bansal, Raj, K.; Shrama, Vino K.; Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry; vol. 31; nb. 8; (1992); p. 521 - 523 View in Reaxys

HO O

H

O

O

O Br

O

O Br

O

racemate

O

Rx-ID: 2690288 View in Reaxys 17/61 Yield

Conditions & References

37 %

With lithium diisopropyl amide in tetrahydrofuran, Time= 0.166667h Guindon, Y.; Yoakim, C.; Gorys, V.; Ogilvie, W. W.; Delorme, D.; et al.; Journal of Organic Chemistry; vol. 59; nb.

5; (1994); p. 1166 - 1178 View in Reaxys

HO O

O

O

O Br

O

Rx-ID: 8583035 View in Reaxys 18/61 Yield

Conditions & References With sodium ethanolate in ethanol, Time= 2h, T= 20 °C , Cyclization Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542 View in Reaxys

N O N H

E

O

O O

Rx-ID: 11799714 View in Reaxys 19/61 Yield

Conditions & References Reaction Steps: 3 1: (4-methoxyphenyl)3P(O); tert-butyl hydroperoxide / Gd(Oi-Pr)3; (S)-6,6'-I-BINOL / tetrahydrofuran; toluene / 12 h / 25 °C 2: 91 percent / DMAP / acetonitrile / 12 h / 20 °C 3: 87 percent / ethanol / 12 h / 20 °C With tert.-butylhydroperoxide, 4-(N,N-dimethlyamino)pyridine, (p-MeOPh)3PO, Gd(Oi-Pr)3, (S)-6,6'-I-BINOL in tetrahydrofuran, ethanol, toluene, acetonitrile Chen, Zhihua; Morimoto, Hiroyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu; Synlett; nb. 20; (2006); p. 3529 3532 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

6/18

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O

O

O

O

O

E

O

O

O

Rx-ID: 39189917 View in Reaxys 20/61 Yield

Conditions & References With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetic acid, acetonitrile, Time= 2h, T= 0 °C , Overall yield = 26 percent; Overall yield = 12 mg; Optical yield = 76 percent ee; enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

O

O

O

O

E

O

O

Rx-ID: 39189918 View in Reaxys 21/61 Yield

Conditions & References With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetic acid, acetonitrile, Time= 2h, T= 0 °C , Overall yield = 30 percent; Overall yield = 10 mg; Optical yield = 70 percent ee; enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

O

O

E

O

O

O O

Rx-ID: 39190054 View in Reaxys 22/61 Yield

Conditions & References With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2 in acetonitrile, Time= 2h, T= 0 °C , Temperature, Overall yield = 57 percent; Optical yield = 86 percent ee; enantioselective reaction Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

O

O

O

O– Na +

O O

O

O

O

racemate

racemate

O racemate

Rx-ID: 9336618 View in Reaxys 23/61 Yield

Conditions & References With sodium hydroxide, N-benzyl-N,N,N-triethylammonium chloride in dichloromethane, T= 10 - 15 °C

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Jonczyk, Andrzej; Zomerfeld, Tomasz; Tetrahedron Letters; vol. 44; nb. 11; (2003); p. 2359 - 2361 View in Reaxys

H

O

O

O

O racemate

Rx-ID: 21309236 View in Reaxys 24/61 Yield

Conditions & References Reaction Steps: 2 1: 1.) LDA / 1.) THF, hexane, -80 deg C, 5 min, 2.) from -80 deg C to room temp.

2: CH2Cl2 With lithium diisopropyl amide in dichloromethane Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212 View in Reaxys Reaction Steps: 2 1: 1.) LDA / 1.) THF, hexane, -80 deg C, 5 min, 2.) 5 min 2: CH2Cl2 With lithium diisopropyl amide in dichloromethane Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212 View in Reaxys

H

O

O

O

O racemate

Rx-ID: 21309237 View in Reaxys 25/61 Yield

Conditions & References Reaction Steps: 2 1: 1.) LDA / 1.) THF, hexane, -80 deg C, 5 min, 2.) from -80 deg C to room temp.

2: CH2Cl2 With lithium diisopropyl amide in dichloromethane Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212 View in Reaxys Reaction Steps: 2 1: 1.) LDA / 1.) THF, hexane, -80 deg C, 5 min, 2.) 5 min 2: CH2Cl2 With lithium diisopropyl amide in dichloromethane Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212 View in Reaxys

H

O

O

O

Br

O

O O

Rx-ID: 2690287 View in Reaxys 26/61 Yield

Conditions & References With sodium ethanolate in benzene, Time= 5h, T= 60 - 65 °C Kuroyan, R. A.; Markosyan, A. I.; Engoyan, A. P.; Vartanyan, S. A.; Journal of Organic Chemistry USSR (English Translation); vol. 19; (1983); p. 1709 - 1714; Zhurnal Organicheskoi Khimii; vol. 19; nb. 9; (1983); p. 1947 - 1953 View in Reaxys

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

8/18

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O O

O

E

O

O O

O O

Rx-ID: 31065411 View in Reaxys 27/61 Yield

Conditions & References With iron(II) trifluoromethanesulfonate, peracetic acid, C48H36N2, acetic acid in acetonitrile, Time= 0.5h, T= 0 °C , Inert atmosphere, enantioselective reaction Nishikawa, Yasuhiro; Yamamoto, Hisashi; Journal of the American Chemical Society; vol. 133; nb. 22; (2011); p.

8432 - 8435 View in Reaxys

O

O

O

O

E

HO

rel-configuration

Rx-ID: 39189932 View in Reaxys 28/61 Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, oxalyl dichloride, C48H36N2, N,N-dimethyl-formamide in diethyl ether, hexane, dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O HO

E O O O rel-configuration

Rx-ID: 39189935 View in Reaxys 29/61 Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, oxalyl dichloride, C48H36N2, N,N-dimethyl-formamide in diethyl ether, hexane, dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

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9/18

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O

O

O

O

E

HO

rel-configuration

Rx-ID: 39189936 View in Reaxys 30/61 Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, oxalyl dichloride, C48H36N2, N,N-dimethyl-formamide in diethyl ether, hexane, dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O HO

E

O O O rel-configuration

Rx-ID: 39189940 View in Reaxys 31/61 Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, oxalyl dichloride, C48H36N2, N,N-dimethyl-formamide in diethyl ether, hexane, dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O O

O

rel-configuration

Rx-ID: 39189956 View in Reaxys 32/61 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether / 1.5 h / 0 - 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

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10/18

2016-02-16 06:19:54

O

O

O

O

E

Cl

rel-configuration

Rx-ID: 39190006 View in Reaxys 33/61 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O E

Cl

O O O rel-configuration

Rx-ID: 39190008 View in Reaxys 34/61 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O Cl

E

O O O rel-configuration

Rx-ID: 39190010 View in Reaxys 35/61 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

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N

O O N H

O

O O

Rx-ID: 11801368 View in Reaxys 36/61 Yield

Conditions & References Reaction Steps: 2 1: 91 percent / DMAP / acetonitrile / 12 h / 20 °C 2: 87 percent / ethanol / 12 h / 20 °C With 4-(N,N-dimethlyamino)pyridine in ethanol, acetonitrile Chen, Zhihua; Morimoto, Hiroyuki; Matsunaga, Shigeki; Shibasaki, Masakatsu; Synlett; nb. 20; (2006); p. 3529 3532 View in Reaxys

H

HI, I2

O

O

O

O

Rx-ID: 15849582 View in Reaxys 37/61 Yield

Conditions & References Reaction Steps: 2 1: N-(p-toluenesulfonyl)-S-valine; BH3*THF / tetrahydrofuran; CH2Cl2 / 15 h / -78 °C 2: NaOEt / ethanol / 2 h / 20 °C With N-(p-toluenesulfonyl)-L-valine, borane-THF, sodium ethanolate in tetrahydrofuran, ethanol, dichloromethane, 1: Addition / 2: Cyclization Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542 View in Reaxys

O

O

Si Br

O

O O

Rx-ID: 15852104 View in Reaxys 38/61 Yield

Conditions & References Reaction Steps: 2 1: N-(p-toluenesulfonyl)-S-valine; BH3*THF / tetrahydrofuran; CH2Cl2 / 15 h / -78 °C 2: NaOEt / ethanol / 2 h / 20 °C With N-(p-toluenesulfonyl)-L-valine, borane-THF, sodium ethanolate in tetrahydrofuran, ethanol, dichloromethane, 1: Addition / 2: Cyclization Kiyooka, Syun-Ichi; Shahid, Kazi A.; Tetrahedron Asymmetry; vol. 11; nb. 7; (2000); p. 1537 - 1542 View in Reaxys

O

O Cl

O O

E

OH

rel-configuration

Rx-ID: 39189909 View in Reaxys 39/61 Yield

Conditions & References Reaction Steps: 2

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12/18

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1: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

E

HO

O

O

O O

O

Rx-ID: 39189933 View in Reaxys 40/61 Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, oxalyl dichloride, C48H36N2, N,N-dimethyl-formamide in diethyl ether, hexane, dichloromethane, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

E

HO

O

O

O O

O

Rx-ID: 39189938 View in Reaxys 41/61 Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, 4-(N,N-dimethlyamino)pyridine, oxalyl dichloride, C48H36N2, triethylamine, N,N-dimethyl-formamide in dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O O

O

HO

E

O

O

O

O

Rx-ID: 39189941 View in Reaxys 42/61

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Yield

Conditions & References Reaction Steps: 3 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 20 °C 2: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 3: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, oxalyl dichloride, C48H36N2, N,N-dimethyl-formamide in diethyl ether, hexane, dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

E

Cl

O

O

O O

O

Rx-ID: 39190007 View in Reaxys 43/61 Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

O

E

Cl

O

O

O O

O

Rx-ID: 39190009 View in Reaxys 44/61 Yield

Conditions & References Reaction Steps: 2 1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, 4-(N,N-dimethlyamino)pyridine, C48H36N2, triethylamine in dichloromethane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O O

O

Cl

E

O

O

O

O

Rx-ID: 39190011 View in Reaxys 45/61

Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.

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Yield

Conditions & References Reaction Steps: 2 1: n-butyllithium / diethyl ether; hexane / 0.25 h / 20 °C 2: C48H36N2; iron(II) trifluoromethanesulfonate; peracetic acid / acetonitrile; acetic acid / 2 h / 0 °C With iron(II) trifluoromethanesulfonate, peracetic acid, n-butyllithium, C48H36N2 in diethyl ether, hexane, acetic acid, acetonitrile Luo, Lan; Yamamoto, Hisashi; European Journal of Organic Chemistry; vol. 2014; nb. 35; (2014); p. 7803 - 7805 View in Reaxys

O

H

O

O Cl

O

O

O

racemate

Rx-ID: 601414 View in Reaxys 46/61 Yield

Conditions & References With sodium amide Valente; Wolfhagen; Journal of Organic Chemistry; vol. 31; (1966); p. 2509,2510,2511 View in Reaxys

O

H

O

O

O

O Br

O

O

O

O racemate

racemate

Rx-ID: 2690286 View in Reaxys 47/61 Yield

Conditions & References With sodium ethanolate in ethanol Alekseeva, L. M.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Journal of Organic Chemistry USSR (English Translation); vol. 22; nb. 9; (1986); p. 1664 - 1666; Zhurnal Organicheskoi Khimii; vol. 22; nb. 9; (1986); p. 1854 - 1857 View in Reaxys

HO

N

O

O

O

O

O

N O

O

O

racemate

racemate

Rx-ID: 1462025 View in Reaxys 48/61 Yield

Conditions & References in dichloromethane, Yield given. Yields of byproduct given. Title compound not separated from byproducts Johnson, Carl R.; Bade, Thomas R.; Journal of Organic Chemistry; vol. 47; nb. 7; (1982); p. 1205 - 1212 View in Reaxys

H O

polymer-PPh2 (1+)-CH2-Ph*Br(1-)

O

O

O

Rx-ID: 18525176 View in Reaxys 49/61 Yield

Conditions & References Reaction Steps: 2 1: 1.) EtMgBr / 1.) THF, -78 deg C, 10 min With ethylmagnesium bromide Satoh; Kitoh; Onda; Takano; Yamakawa; Tetrahedron; vol. 50; nb. 17; (1994); p. 4957 - 4972 View in Reaxys

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O

HO

N

O

O

N O

O

Rx-ID: 1462024 View in Reaxys 50/61 Yield

Conditions & References Satoh; Kitoh; Onda; Takano; Yamakawa; Tetrahedron; vol. 50; nb. 17; (1994); p. 4957 - 4972 View in Reaxys

H O

O

Br

O

O

O O

Rx-ID: 2690294 View in Reaxys 51/61 Yield

Conditions & References Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314 View in Reaxys

O

H O

O

Br

O

O

O

O O racemate

O

Rx-ID: 2678756 View in Reaxys 52/61 Yield

Conditions & References Anisimova, O. S.; Chistyakov, V. V.; Bokanov, A. I.; Shvedov, V. I.; Sheinker, Yu. N.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 22; nb. 10; (1986); p. 1058 - 1063; Khimiya Geterotsiklicheskikh Soedinenii; vol. 22; nb. 10; (1986); p. 1310 - 1314 View in Reaxys

Cl O

OH

O

potassium hydroxide

O

O HO

O

Rx-ID: 7155934 View in Reaxys 53/61 Yield

Conditions & References Richard; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 199; (1934); p. 71 View in Reaxys

O

O

O

Rx-ID: 5469018 View in Reaxys 54/61 Yield

Conditions & References α-Methyl-zimtsaeure-aethylester, Peroxyessigsaeure in E. Patent; Union Carbide Corp.; US3141027; (1959); GB863446; ; nb. 25982; (1961) View in Reaxys Benzaldehyd, 2-Halogenpropionsaeure-aethylester (Na-aethylat) n. Darzens Martynow; Below; J. Gen. Chem. USSR (Engl. Transl.); vol. 32; (1962); p. 2341,2308 View in Reaxys aus entspr. ungesaett.Verb., m-Chlorperbenzoesaeure

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Kagan et al.; Journal of Organic Chemistry; vol. 41; (1976); p. 2355,2361 View in Reaxys Ib, PhCHO Villieras,J. et al.; Journal of Organometallic Chemistry; vol. 42; (1972); p. C5 - C8 View in Reaxys

O

O

O racemate

Rx-ID: 5435403 View in Reaxys 55/61 Yield

Conditions & References aus trans-α-Methylzimtsaeureaethylester, m-Chlorperbenzoesaeure Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145 View in Reaxys

O

O

2H

O

Rx-ID: 6535742 View in Reaxys 56/61 Yield

Conditions & References aus Deuteriobenzaldehyd (2b), 2-Brompropionsaeureaethylester, NaOEt/A. Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145 View in Reaxys

O

O

O racemate

Rx-ID: 8396392 View in Reaxys 57/61 Yield

Conditions & References aus Gemisch der Glycidester (1a), KOH Kagan; Firth; Journal of Organic Chemistry; vol. 39; (1974); p. 3145 View in Reaxys

O

O

O racemate

Rx-ID: 8397330 View in Reaxys 58/61 Yield

Conditions & References aus Benzaldehyd, Bromester (1c), NaH (Tab.) Dagli; Wemple; Journal of Organic Chemistry; vol. 39; (1974); p. 2938 View in Reaxys

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O

O

O racemate

Rx-ID: 8397331 View in Reaxys 59/61 Yield

Conditions & References aus Benzaldehyd, Bromester (1c), NaH (Tab.) Dagli; Wemple; Journal of Organic Chemistry; vol. 39; (1974); p. 2938 View in Reaxys

O

O

O

Rx-ID: 5452332 View in Reaxys 60/61 Yield

Conditions & References Benzaldehyd, CH3-CHCl-CO2-CH3, NaH/HMPT, 20grad Roux-Schmitt et al.; Tetrahedron; vol. 28; (1972); p. 4965,4968, 4975 View in Reaxys

O

O

O

Rx-ID: 6532976 View in Reaxys 61/61 Yield

Conditions & References aus Me-CHCl-CO-O-t-Bu (4b), PhCHO in CH2Cl2/NaOH/Bu4NBr d'Incan; Seyden-Penne; Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques; vol. 281; (1975); p. 1031 View in Reaxys

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