Intramolecular S(N)2 reaction at alpha-carbon of trifluoromethyl group: preparation of optically active 2-trifluoromethylaziridine

被引：43

作者：

Katagiri, T

Ihara, H

Takahashi, M

Kashino, S

Furuhashi, K

Uneyama, K

机构：

[1] OKAYAMA UNIV,FAC ENGN,DEPT APPL CHEM,OKAYAMA 700,JAPAN

[2] OKAYAMA UNIV,FAC SCI,DEPT CHEM,OKAYAMA 700,JAPAN

[3] JAPAN ENERGY CORP,PHARMACEUT & BIOTECHNOL LAB,TODA,SAITAMA 335,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1997年 / 8卷 / 17期

关键词：

D O I：

10.1016/S0957-4166(97)00320-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

We have succeeded in intramolecular nucleophilic substitution of the hydroxyl group in (S)-1-(alkylamino)-3,3,3-trifluoro-2-propanol. The reaction provides an optically pure (R)-1-benzyl-2-trifluoromethylaziridine in good yield from optically pure (S)-3-(benzylamino)-1,1,1-trifluoro-2-propanol, which was prepared from (S)-3,3,3-trifluoropropene oxide (75% ee). (C) 1997 Published by Elsevier Science Ltd.

引用

页码：2933 / 2937

页数：5

共 14 条

[1] [Anonymous], 1991, Fluorine in Bioorganic Chemistry
[2] NEW AZIRIDINE SYNTHESIS
APPEL, R
KLEINSTU.R
[J]. CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (01): : 5 - 12
[3] Bussche-Hunnefeld C. V. D., 1992, CHEM BER, V125, P2795, DOI DOI 10.1002/CBER.19921251227
[4] FURUHASHI K, 1992, CHIRALITY IND, P167
[5] Functional group transformation of alpha-trifluoromethylated alcohol derivatives
Hagiwara, T
Tanaka, K
Fuchikami, T
[J]. TETRAHEDRON LETTERS, 1996, 37 (45) : 8187 - 8190
[6] Hudlicky M., 1995, CHEM ORGANIC FLUORIN, V1st
[7] KATAGIRI T, 1996, Patent No. 0827044
[8] KLAUBUNDE KJ, 1972, J AM CHEM SOC, V94, P5985
[9] Kukhar VP., 1995, FLUORINE CONTAINING
[10] A NEW SYNTHESIS OF AZIRIDINES FROM BETA-AMINO ALCOHOLS WITH TRIPHENYLPHOSPHINE DIBROMIDE
OKADA, I
ICHIMURA, K
SUDO, R
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1970, 43 (04) : 1185 - +

← 1 2 →