A General Method for the Reductive Carbamation and Sulfonamidation of Aldehydes

Michael D. Alexander, Robert E. Anderson, Joseph Sisko, Steven M. Weinreb

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22 Scopus citations

Abstract

The reductive amination of aldehydes and ketones is a very important method for the synthesis and homologation of amines.1 The success of this methodology is based on the facile reaction of amines and ammonia with carbonyl compounds to form imines or iminium salts, which in turn are readily reduced by a variety of reagents. The corresponding transformation of amides and related compounds is much rarer and has found relatively little synthetic use to date.2 The difficulty with effecting is due to the low nucleophilicity of amido compounds which inhibits imine formation. Moreover, imines bearing electron-withdrawing groups on nitrogen tend to be unstable and usually tautomerize or oligomerize.

Original languageEnglish (US)
Pages (from-to)2563-2564
Number of pages2
JournalJournal of Organic Chemistry
Volume55
Issue number8
DOIs
StatePublished - Jan 1 1990

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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