Highly diastereoselective anti-aldol reactions of glycolate titanium enolates

J Org Chem. 2009 Feb 20;74(4):1788-90. doi: 10.1021/jo8025466.

Abstract

Diastereoselective aldol reactions of enolates of alpha-hydroxy ester with different aldehydes are metal tunable, providing either anti- or syn- products. The highest anti-selectivities were obtained with TiCl(OiPr)(3), while Ti(OiPr)(4) provides the opposite syn-products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry*
  • Aldehydes / chemistry*
  • Chelating Agents / chemistry
  • Glycolates / chemistry*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism
  • Substrate Specificity
  • Titanium / chemistry*

Substances

  • Alcohols
  • Aldehydes
  • Chelating Agents
  • Glycolates
  • Organometallic Compounds
  • glycolic acid
  • Titanium