Stanna-Brook rearrangement of carboxylic acid derivatives. Synthetic utility and mechanistic studies

Article abstract of DOI:10.1021/ol049826m

(Equation presented) The reaction of R₃SnLi with carboxylic acid derivatives proceeds through a novel, very fast stanna-Brook rearrangement that generates α-alkoxyorganolithium compounds as intermediates. The outcome of these reactions depends on the nature of the carboxyl derivatives. Reaction of R₃SnLi with ester derivatives gives rise to coupled products through a novel C-C bond formation reaction. Experimental evidence of the detailed reaction mechanism is provided.