A direct and general method for the reductive alkylation of tertiary lactams/amides: application to the step economical synthesis of alkaloid (−)-morusimic acid D

KJ Xiao, Y Wang, YH Huang, XG Wang…

Index: Xiao, Kai-Jiong; Wang, Yu; Huang, Ying-Hong; Wang, Xiao-Gang; Huang, Pei-Qiang Journal of Organic Chemistry, 2013 , vol. 78, # 17 p. 8305 - 8311

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Citation Number: 25

Abstract

Full details of the direct and general method for the reductive alkylation of tertiary lactams and amides to give tertiary sec-alkylamines are presented. This one-pot method consists of in situ activation of a lactam or an amide with Tf2O/DTBMP, addition of a Grignard reagent, and reduction of the resulting iminium intermediates. Alkyl, benzyl, and aryl Grignard reagents and several reductants or reducing conditions (LiAlH4, NaBH4, Hantzsch ester, ...

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