Tandem radical addition–aldol condensations: evidence for the formation of zinc enolates in diethylzinc mediated radical additions to N-enoyloxazolidinones

Abstract

Diethylzinc mediated addition of alkyl radicals to chiral N-enoyloxazolidinones is immediately followed by homolytic substitution at zinc leading to a zinc enolate; the trapping of the latter in a subsequent aldol condensation serves as a useful mechanistic probe; overall this reaction sequence constitutes a novel example of a one pot, three-component, radical-polar crossover reaction.