Rapid access to polyketide scaffolds via vinylogous Mukaiyama aldol reactions

Org Lett. 2001 Nov 1;3(22):3561-4. doi: 10.1021/ol016677o.

Abstract

[reaction: see text]. The use of the Z-configured vinylogous silyl ketene acetals in Mukaiyama aldol reactions is described. Isopropyl alcohol as scavanger and the use of tris(pentafluorophenyl)borane as the Lewis acid are required for obtaining the gamma-alkylated syn-product selectively. In cases of alpha-chiral aldehydes, Felkin-Anh selectivity was observed.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Propanol
  • Acetals / chemistry*
  • Aldehydes / chemistry
  • Boranes
  • Catalysis
  • Ethylenes / chemistry*
  • Indicators and Reagents
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Stereoisomerism

Substances

  • Acetals
  • Aldehydes
  • Boranes
  • Ethylenes
  • Indicators and Reagents
  • Ketones
  • ketene
  • 2-Propanol