Stereoselective synthesis of 1,2-amino alcohols by addition of organocuprate center-dot BF3 complexes and organolithium reagents to an alpha-silyloxyaldimine derived from (S)-ethyl lactate

被引：32

作者：

Ishimaru, K ^{[1
]}

Tsuru, K ^{[1
]}

Yabuta, K ^{[1
]}

Wada, M ^{[1
]}

Yamamoto, Y ^{[1
]}

Akiba, K ^{[1
]}

机构：

[1] HIROSHIMA UNIV, FAC SCI, DEPT CHEM, HIGASHIHIROSHIMA 739, JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 41期

关键词：

D O I：

10.1016/0040-4020(96)00776-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,2-Amino alcohols were synthesized by addition of organocuprate . BF3 2 (R=n-Bu, n-octyl, Me, phenethyl, Ph), organocopper . BF3 3 (R=Me, n-Bu), and organolithiums (R=n-Bu, n-octyl, Me, phenethyl, Ph) to an alpha-silyloxyaldimine 1 derived from commercially available (S)-ethyl lactate. The reactions with organocuprate . BF3 2 and organocopper . BF3 3 led to the anti isomers almost exclusively (anti:syn=>98:<2 for R=n-Bu, n-octyl, Me, phenethyl and anti:syn=95:5 for R=Ph, 52-93% isolated yields) and the syn isomers could be obtained with high stereoselectivities by using organolithiums (anti:syn=10:90-20:80, 41-71% isolated yields). Copyright (C) 1996 Elsevier Science Ltd.

引用

页码：13137 / 13144

页数：8

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