Condensation of laterally lithiated o-methyl and o-ethyl benzamides with imines mediated by (-)-sparteine.: Enantioselective synthesis of tetrahydroisoquinolin-1-ones

被引：38

作者：

Derdau, V ^{[1
]}

Snieckus, V ^{[1
]}

机构：

[1] Queens Univ, Dept Chem, Kingston, ON K7L 3N6, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 06期

关键词：

D O I：

10.1021/jo001369+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first asymmetric synthesis of tetrahydroisoquinolin-1-ones using a (-)-sparteine-mediated lateral metalation-imine addition sequence to furnish 3-phenyl tetrahydroisoquinolinones 3a with enantioselectivities up to 81% ee is described (Scheme 4). For amide 7b, imine addition products 10 and 11 have been obtained with high diastereoselectivities (91-97% de) and enantioselectivities (91-98% ee) (Scheme 8).

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页码：1992 / 1998

页数：7

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