Diastereoselective, vinylogous mukaiyama aldol additions of silyloxy furans to cyclic ketones: annulation of butenolides and gamma-lactones

Org Lett. 2006 Jul 6;8(14):2909-12. doi: 10.1021/ol060534q.

Abstract

[reaction: see text] Vinylogous Mukaiyama aldol reactions employing silyloxyfurans and substituted cyclic ketones are described. These annulations proceed with moderate to good diastereoselectivity. The potential application of this process to the synthesis of butenolide and gamma-lactone containing natural products was demonstrated by further transformations of the addition products.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • Catalysis
  • Furans / chemical synthesis
  • Furans / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Molecular Structure
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Furans
  • Ketones
  • Lactones
  • Silanes
  • butenolide
  • 4-Butyrolactone