Highly selective α-acylvinyl anion additions to imines

Troy E. Reynolds*, Michael S. Binkley, Karl A. Scheidt

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

α-Hydroxypropargylsilanes undergo rearrangement to form reactive lithium allenolates. The resulting ∞-acylvinyl anion equivalents undergo highly selective additions to N-tert-butanesulfinyl imines generating/β- substituted aza-MBH-type products. High yields are achieved for a wide range of α-hydroxypropargylsilanes as well as for a diverse selection of imines. The reactions proceed with good to excellent diastereoselectivity and regioselectivity (8-20:1 major/Σ minor) favoring the Z-isomer of the alkene.

Original languageEnglish (US)
Pages (from-to)5227-5230
Number of pages4
JournalOrganic Letters
Volume10
Issue number22
DOIs
StatePublished - Dec 1 2008

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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