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

Nicholas M. Leonard, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)6915-6923
Number of pages9
JournalJournal of Organic Chemistry
Volume74
Issue number18
DOIs
StatePublished - Sep 18 2009

ASJC Scopus subject areas

  • Organic Chemistry

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