Stereocontrol at the quaternary center in 1-substituted 1-phenyl-2,2,2-trifluoroethylamines:: Stereospecific substitution with retention of a chiral cyclic fluoral N,O-acetal with organolithium reagents

被引：51

作者：

Ishii, A

Miyamoto, F

Higashiyama, K ^{[1
]}

Mikami, K

机构：

[1] Hoshi Univ, Fac Pharmaceut Sci, Shinagawa Ku, Tokyo 142, Japan

[2] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 152, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 10期

关键词：

D O I：

10.1016/S0040-4039(97)10840-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric synthesis of 1-substituted 1-phenyl-2,2,2-trifluoroethylamines from chiral 1,3-oxazolidines is described. The stereospecific substitution reaction with organolithium reagents of chiral 1,3-oxazolidines having a trifluoromethyl group proceeds with retention to control the newly created quaternary center. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：1199 / 1202

页数：4

共 30 条

[1] CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS
ALEXAKIS, A
MANGENEY, P
[J]. TETRAHEDRON-ASYMMETRY, 1990, 1 (08) : 477 - 511
[2] STUDIES ON THE MECHANISM AND ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS
DENMARK, SE
ALMSTEAD, NG
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) : 8089 - 8110
[3] RING-CHAIN TAUTOMERISM OF 1,3-OXAZOLIDINES PREPARED FROM NOREPHEDRINE AND NORPSEUDOEPHEDRINE
FULOP, F
BERNATH, G
MATTINEN, J
PIHLAJA, K
[J]. TETRAHEDRON, 1989, 45 (13) : 4317 - 4324
[4] Functional group transformation of alpha-trifluoromethylated alcohol derivatives
Hagiwara, T
Tanaka, K
Fuchikami, T
[J]. TETRAHEDRON LETTERS, 1996, 37 (45) : 8187 - 8190
[5] HAYASHI T, 1994, TETRAHEDRON-ASYMMETR, V5, P955
[6] Asymmetric synthesis of chiral fluorinated compounds using N-acyloxazolidinones
Iseki, K
Kobayashi, Y
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1996, 54 (02) : 122 - 131
[7] REVERSAL OF STEREOSELECTIVITY IN THE EVANS ALDOL REACTION OF ALPHA,ALPHA-DIFLUORO AND ALPHA,ALPHA,ALPHA-TRIFLUORO CARBONYL-COMPOUNDS
ISEKI, K
OISHI, S
TAGUCHI, T
KOBAYASHI, Y
[J]. TETRAHEDRON LETTERS, 1993, 34 (50) : 8147 - 8150
[8] HIGHLY DIASTEREOSELECTIVE ACETAL CLEAVAGES USING NOVEL REAGENTS PREPARED FROM ORGANOALUMINUM AND PENTAFLUOROPHENOL
ISHIHARA, K
HANAKI, N
YAMAMOTO, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (23) : 10695 - 10704
[9] KITAZUME T, 1993, FLUORINE CHEM
[10] ASYMMETRIC ENE REACTION CATALYZED BY CHIRAL ORGANO-ALUMINUM REAGENT
MARUOKA, K
HOSHINO, Y
SHIRASAKA, T
YAMAMOTO, H
[J]. TETRAHEDRON LETTERS, 1988, 29 (32) : 3967 - 3970

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