Reaction of allylzinc reagents and zinc enolates of ketones with alpha-amidoalkylphenyl sulfones.
Alpha-amidoalkylphenyl sulfones behave as N-acylimino equivalents in the reaction with functionalized allylzinc reagents. The addition products obtained using the zinc derivative of ethyl 2-(bromomethyl)acrylate can be readily transformed into alpha-methylene-gamma-lactams using different cyclization procedures. The allylzinc reagent obtained from 3-bromo-1-acetoxy-1-propene directly affords protected 1,2-amino alcohols with a preference for the anti stereoisomer, regardless of the structure of the alpha-amidoalkylphenyl sulfone employed. This procedure can be extended to the use of zinc enolates obtained from alpha-bromo ketones and leads to the synthesis of N-protected beta-amino ketones.
Petrini
Marino
M
Dipartimento di Scienze Chimiche, Università di Camerino, via S. Agostino, 1. I-62032 Camerino, Italy. marino.petrini@unicam.it
Profeta
Roberto
R
Righi
Paolo
P