Chiral oxazolidinones from α-hydroxy oxazolidines:: a new access to 1,2-amino alcohols

被引：14

作者：

Agami, C ^{[1
]}

Amiot, F ^{[1
]}

Couty, F ^{[1
]}

Dechoux, L ^{[1
]}

Kaminsky, C ^{[1
]}

Venier, O ^{[1
]}

机构：

[1] Univ Paris 06, Lab Synth Asymetr, UMR 7611, CNRS, F-75005 Paris, France

来源：

TETRAHEDRON-ASYMMETRY | 1998年 / 9卷 / 22期

关键词：

D O I：

10.1016/S0957-4166(98)00414-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

N-Carbamoyl-alpha-hydroxy oxazolidines prepared from N-Boc-2-acyl oxazolidines or N-Boc-2-alkenyl oxazolidines, using phenyl glycinol as the chiral source, are converted into bicyclic oxazolidinones. Reactions of these compounds with different nucleophiles under conditions suitable for the production of N-acyliminium ions were studied. Allylsilane reacted very stereoselectively in all cases, and this reaction provides a new flexible entry for the preparation of enantiopure syn-2-amino alcohols, possibly bearing an additional stereocenter ex to the hydroxyl moiety. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3955 / 3958

页数：4

共 17 条

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