Tetrahedron letters

A facile route to α-imino acetals and the corresponding monoacetal derivatives of α-diketones with complete regiochemical control.

JH Babler, CJ Marcuccilli

Index: Babler, James H.; Marcuccilli, Charles J. Tetrahedron Letters, 1987 , vol. 28, # 40 p. 4657 - 4660

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Citation Number: 5

Abstract

ABSTRACT: Treatment of representative orthoesters (2) with pyruvonitrile (3) afforded the corresponding o, a-diethoxynitriles(4) in 65-80% yields. Depending upon the conditions used to protonate the initial adduct, subsequent addition of an organolithium(5) or Grignard reagent to the latter (4) led to the obtention of either a-imino acetals (6) or the corresponding monoprotected a-diketones (_Z) in> 90% yield.