Room-temperature highly diastereoselective Zn-mediated allylation of chiral N-tert-butanesulfinyl imines:: Remarkable reaction condition controlled stereoselectivity reversal

被引：124
作者：
Sun, Xing-Wen
Xu, Ming-Hua
Lin, Guo-Qiang
机构：
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai, Peoples R China
来源：
ORGANIC LETTERS | 2006年 / 8卷 / 21期
关键词：
D O I：
10.1021/ol062216x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient method for the highly diastereoselective synthesis of chiral homoallylic amines by Zn-mediated allylation of chiral N-tert-butanesulfinyl imines at room temperature was developed. By simply tuning the reaction conditions, the method allows the achievement of a highly remarkable opposite stereocontrol, affording the desired stereochemical outcome in good yield and with excellent diastereoselectivity (up to 98% dr). With N-sulfinyl ketimines, the corresponding quaternary carbon-containing chiral homoallylic amines could also be produced.
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收藏
页码：4979 / 4982
页数：4
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