Trimethylsilyl triflate promoted addition of allyltributylstannanc to aldonitrones; one-pot synthesis of 5-iodomethylisoxazolidines

Article abstract of DOI:10.1016/S0040-4039(97)10862-0

the trimethylsilyl triflate promoted allylation of nitrones with allyltributylstannane affords O-silylated hydroxylamines in high yield; when the crude reaction mixture is quenched with N-iodosuccinimide, 5-iodomethylisoxazolidines are formed in excellent yields. The overall one-pot two-step process represents a valuable improvement in terms of time, cost and overall yield with respect to the previously reported three stage procedure involving nitrone allylation, hydroxylamine O-silylation, and iodocyclisation.