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
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.
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页码:3955 / 3958
页数:4
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