Orthoacylimines: A new class of chiral auxiliaries for nucleophilic addition of organolithium reagents to imines

被引:24
作者
Boezio, AA [1 ]
Solberghe, G [1 ]
Lauzon, C [1 ]
Charette, AB [1 ]
机构
[1] Univ Montreal, Dept Chim, Stn Downtown, Montreal, PQ H3C 3J7, Canada
关键词
D O I
10.1021/jo026571m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new class of orthoacylimine-derived chiral auxiliaries has been synthesized and tested in the nucleophilic addition of organolithium reagents to imines. The precursors can be prepared by an aza-Wittig reaction between the corresponding orthoacyl azide and a variety of aldehydes in the presence of trialkylphosphines. The nucleophilic addition of organolithium reagents led to the addition products in good yields and with good to excellent diastereoselectivities (from 85:15 to 99:1). The chiral, nonracemic secondary amines could be readily obtained under mild hydrolytic condition. Furthermore, the chiral auxiliary can be recovered in quantitative yield and reconverted to the starting orthoacyl azide precursor. This method was applied to the synthesis of (S)-t-leucine.
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页码:3241 / 3245
页数:5
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