PREPARATION OF PRIMARY AMINES VIA N-DIISOBUTYLALUMINUM IMINES

The importance of the azomethine group in organic synthesis is well documented1. Davis and Mancinelli2 have demonstrated the usefulness of “masked” imine derivatives of ammonia in the synthesis of secondary and tertiary carbinamines from enolizable and nonenolizable sulfen-imines. More recently metalloimines have found application in the synthesis of 0-lactams through the reaction with ester enolates.3 N-Trimethylsilyl imines have been also utilized by Hart in the synthesis of primary amines.4a The use of N-trimethylsilyl imines, however, is generally restricted to nonenolizable aldimines since it has been reported4a that the enolizable ones, upon reaction with alkyllithium or Grignard reagents, give poor yields of the expected amines due to a competitive enolization reaction of the starting material. © 1990, American Chemical Society. All rights reserved.