Catalytic redox-initiated glycolate aldol additions of silyl glyoxylates

Org Lett. 2009 Feb 19;11(4):827-30. doi: 10.1021/ol802828d.

Abstract

Lanthanide triisopropoxides catalyze a rapid, tandem MPV reduction/Brook rearrangement/aldol sequence between silyl glyoxylates and aldehydes that achieves catalytic turnover through alkoxide transfer from a strain-release Lewis acidic silacycle.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Glyoxylates / chemistry*
  • Lanthanoid Series Elements / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Silanes / chemistry*

Substances

  • Aldehydes
  • Glyoxylates
  • Lanthanoid Series Elements
  • Silanes
  • 3-hydroxybutanal