Formation of medium-sized nitrogen heterocycles from gamma-silyloxy-gamma-lactams

Abstract

Nitrogen heterocycles can be prepared by performing ring-expansion reactions of gamma-silyloxy-gamma-lactams, which are available by the annulation reactions of allylic silanes. Nucleophilic substitution of the annulation products and subsequent translactamization of nitrogen-tethered gamma-lactams provide six-, seven-, and eight-membered ring lactams. An enantiomerically enriched delta-lactam formed from this method was elaborated to form the hydroxypiperidine core structure of the pseudodistomin alkaloids.