α-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 α-methylene-γ -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 α-amidoalkylphenyl sulfone employed. This procedure can be extended to the use of zinc enolates obtained from α-bromo ketones and leads to the synthesis of N-protected β-amino ketones.
Petrini M., Profeta R., Righi P. (2002). Reaction of allylzinc reagents and zinc enolates of ketones with α-amidoalkylphenyl sulfones. JOURNAL OF ORGANIC CHEMISTRY, 67(13), 4530-4535 [10.1021/jo025606f].
Reaction of allylzinc reagents and zinc enolates of ketones with α-amidoalkylphenyl sulfones
Righi P.
2002
Abstract
α-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 α-methylene-γ -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 α-amidoalkylphenyl sulfone employed. This procedure can be extended to the use of zinc enolates obtained from α-bromo ketones and leads to the synthesis of N-protected β-amino ketones.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
