Highly selective acetate aldol additions using mesityl-substituted chiral auxiliaries

Org Lett. 2007 Jan 4;9(1):149-52. doi: 10.1021/ol062688b.

Abstract

[reaction: see text] Highly diastereoselective acetate aldol additions using chlorotitanium enolates of mesityl-substituted N-acetyloxazolidinethione and N-acetylthiazolidinethione auxiliaries are reported. These additions proceed in high yields and diastereoselectivities (93:7 to 98:2) for aliphatic, aromatic, and ,-unsaturated aldehydes. Double diastereoselective acetate aldol additions are also reported and are found to proceed in high yields and diastereoselectivities (90:10 to 97:3).

Publication types

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

MeSH terms

  • Acetates / chemistry*
  • Aldehydes / chemistry*
  • Chromatography, High Pressure Liquid
  • Molecular Structure
  • Oxazolidinones / chemistry
  • Stereoisomerism
  • Thiazolidines / chemistry

Substances

  • Acetates
  • Aldehydes
  • Oxazolidinones
  • Thiazolidines
  • thiazoline-2-thione
  • 3-hydroxybutanal