Highly stereoselective synthesis of substituted γ-lactams from acylsilanes

Robert B. Lettan, Chase C. Woodward, Karl A. Scheidt

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

(Chemical Presented) It takes three : The stereoselective synthesis of highly substituted γ-lactams from amide enolates, acylsilanes, and imines is reported. This multicomponent reaction accesses γ-amino-β-hydroxy amides in a single flask with good yields and excellent levels of diastereoselectivity (see scheme). Exposure of the linear products to microwave irradiation and acidic conditions promotes a cyclization to form the corresponding γ-lactams in excellent yields.

Original languageEnglish (US)
Pages (from-to)2294-2297
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number12
DOIs
StatePublished - Mar 7 2008

Keywords

  • Acylsilanes
  • Chiral auxiliaries
  • Homoenolates
  • Synthetic methods
  • γ-lactams

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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