Diastereodivergent aldol reactions of beta-alkoxy ethyl ketones: modular access to (1,4)-syn and -anti polypropionates

Org Lett. 2008 Aug 21;10(16):3521-4. doi: 10.1021/ol801292t. Epub 2008 Jul 17.

Abstract

Asymmetric substrate-controlled aldol reactions of ethyl ketones of type 4 with aldehyde 3 are reported. Modular access to all possible syn- and anti-aldol products was obtained by careful choice of reaction conditions. To achieve good selectivities in this diastereodivergent approach, selection of the protective group on the beta-oxygen of the enolate (R (2)) was of critical importance.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry
  • Ketones / chemistry*
  • Molecular Structure
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Propionates / chemical synthesis*
  • Propionates / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Ketones
  • Polymers
  • Propionates
  • 3-hydroxybutanal