Formation of Medium-Sized Nitrogen Heterocycles from γ-Silyloxy-γ-Lactams Nicholas M. Leonard K. A. Woerpel 10.1021/jo900869k.s004 https://acs.figshare.com/articles/journal_contribution/Formation_of_Medium_Sized_Nitrogen_Heterocycles_from_Silyloxy_Lactams/2826997 Nitrogen heterocycles can be prepared by performing ring-expansion reactions of γ-silyloxy-γ-lactams, which are available by the annulation reactions of allylic silanes. Nucleophilic substitution of the annulation products and subsequent translactamization of nitrogen-tethered γ-lactams provide six-, seven-, and eight-membered ring lactams. An enantiomerically enriched δ-lactam formed from this method was elaborated to form the hydroxypiperidine core structure of the pseudodistomin alkaloids. 2009-09-18 00:00:00 annulation reactions hydroxypiperidine core structure annulation products Nucleophilic substitution pseudodistomin alkaloids lactam allylic silanes