Oxazolidine ring opening and lsomerization to (E)-imines.: Asymmetric synthesis of aryl-α-fluoroalkyl amino alcohols

被引：50

作者：

Gosselin, F

Roy, A

O'Shea, PD

Chen, CY

Volante, RP

机构：

[1] Merck Frosst Ctr Therapeut Res, Dept Proc Res, Kirkland, PQ H9H 3L1, Canada

[2] Merck Res Labs, Dept Proc Res, Rahway, NJ 07065 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 04期

关键词：

D O I：

10.1021/ol036486g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A base-induced ring opening/imine isomerization/diastereoselective organometallic addition sequence on 4-substituted 2-perfluoroalkyl-1,3-oxazolidines has been developed for the asymmetric synthesis of aryl alpha-perfluoroalkylamine derivatives. This practical method provides chiral amino alcohols in 60-95% yield with uniformely high diastereoselectivities ranging from 35:1 to >100:1.

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页码：641 / 644

页数：4

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