Copper(II)-bis(oxazoline) catalyzed asymmetric Diels-Alder reaction with alpha'-arylsulfonyl enones as dienophiles

J Org Chem. 2008 Aug 15;73(16):6389-92. doi: 10.1021/jo8009227. Epub 2008 Jul 23.

Abstract

Alpha'-arylsulfonyl enones are efficient bidentate dienophiles for the Cu(II)-bis(oxazoline) catalyzed enantioselective Diels-Alder reaction with a number of dienes, affording the corresponding products with good to high enantiomeric excesses. The resulting products can be alkylated and the sulfone removed, so alpha'-arylsulfonyl enones can be regarded as surrogates of simple monodentate enones, which are poor dienophiles with this catalytic system.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Copper / chemistry*
  • Ketones / chemistry*
  • Organometallic Compounds / chemistry
  • Oxazoles / chemistry*
  • Polyenes / chemistry
  • Stereoisomerism
  • Sulfones / chemistry*

Substances

  • Ketones
  • Organometallic Compounds
  • Oxazoles
  • Polyenes
  • Sulfones
  • Copper