Synthesis of tertiary β-hydroxy amides by enolate additions to acylsilanes

Robert B. Lettan, Troy E. Reynolds, Chris V. Galliford, Karl A Scheidt*

*Corresponding author for this work

Research output: Contribution to journalArticle

30 Scopus citations

Abstract

The synthesis of tertiary β-hydroxy amides from acylsilanes, acetamides, and electrophiles is described. The addition of amide enolates to acylsilanes generates β-silyloxy homoenolate reactivity by undergoing a 1,2-Brook rearrangement. These unique nucleophiles formed in situ can then undergo smooth addition to alkyl halides, aldehydes, and ketones. Enolates derived from amides are crucial for the success of this process since ketone enolates suffer from internal return of the β-carbanion onto the carbonyl carbon. The use of optically active amide enolates delivers β-hydroxy amide products with good levels of diastereoselectivity (≥10:1).

Original languageEnglish (US)
Pages (from-to)15566-15567
Number of pages2
JournalJournal of the American Chemical Society
Volume128
Issue number49
DOIs
StatePublished - Dec 13 2006

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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