Lewis acid-Lewis base catalyzed enantioselective hetero-Diels-Alder reaction for direct access to delta-lactones

Org Lett. 2008 May 15;10(10):2019-22. doi: 10.1021/ol800742d. Epub 2008 Apr 23.

Abstract

A complex formed in situ from Er(OTf)3 and a simple commercially available norephedrine ligand promotes an unprecedented [4 + 2] cycloaddition of alpha,beta-unsaturated acid chlorides with a broad range of aromatic and heteroaromatic aldehydes by a cooperative bifunctional Lewis acid-Lewis base catalytic mode of action providing valuable delta-lactone building blocks with excellent enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Erbium / chemistry*
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Ligands
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Lactones
  • Ligands
  • Organometallic Compounds
  • Erbium