Stanna-Brook rearrangement of carboxylic acid derivatives. Synthetic utility and mechanistic studies.
[reaction: see text] The reaction of R(3)SnLi with carboxylic acid derivatives proceeds through a novel, very fast stanna-Brook rearrangement that generates alpha-alkoxyorganolithium compounds as intermediates. The outcome of these reactions depends on the nature of the carboxyl derivatives. Reaction of R(3)SnLi 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.
Paleo
M Rita
MR
Departamento de Química Orgánica, Facultad de Química, Universidad de Santiago de Compostela, 15782 Santiago de Compostela, Spain.
Calaza
M Isabel
MI
Graña
Paula
P
Sardina
F Javier
FJ