Trimethylsilyl triflate promoted addition of allyltributylstannane to aldonitrones; One-pot synthesis of 5-iodomethylisoxazolidines

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. (C) 1998 Elsevier Science Ltd. All rights reserved.