The Journal of organic chemistry

Copper-catalyzed cross-coupling of imines, acid chlorides, and organostannanes: A multicomponent synthesis of α-substituted amides

DA Black, BA Arndtsen

Index: Black, Daniel A.; Arndtsen, Bruce A. Journal of Organic Chemistry, 2005 , vol. 70, # 13 p. 5133 - 5138

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Citation Number: 34

Abstract

A copper-catalyzed cross-coupling of organotin reagents with imines and acid chlorides is reported. The reaction proceeds efficiently with a range of vinyl-, alkyl-, aryl-and heteroaryl- substituted organostannanes as well as a diverse set of imines of non-enolizable aldehydes. Use of chloroformates also allows for the formation of N-protected α-substituted amines. This chemistry has been applied to the synthesis of isoquinoline alkaloid derivatives through ...