Catalyst-controlled diastereoselective hetero-Diels-Alder reactions

Org Lett. 2002 May 16;4(10):1795-8. doi: 10.1021/ol0258785.

Abstract

[reaction: see text] The diastereoselective hetero-Diels-Alder reaction between Danishefsky's diene and chiral aldehydes is catalyzed by chiral chromium-Schiff base complexes. High levels of catalyst control are obtained in several cases, allowing access to all four stereoisomeric products through appropriate choice of aldehyde and catalyst enantiomers.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aldehydes
  • Catalysis
  • Cyclization
  • Indicators and Reagents
  • Pyrans / chemical synthesis*
  • Schiff Bases
  • Stereoisomerism

Substances

  • Aldehydes
  • Indicators and Reagents
  • Pyrans
  • Schiff Bases
  • lactaldehyde