Pd(II)/(t)Bu-quinolineoxazoline: an air-stable and modular chiral catalyst system for enantioselective oxidative cascade cyclization

Org Lett. 2009 Dec 17;11(24):5626-8. doi: 10.1021/ol902348t.

Abstract

An air-stable and structurally tunable chiral (t)Bu-quinolineoxazoline/Pd(II) catalyst system has been developed for the enantioselective oxidative cascade cyclization of a variety of disubstituted olefinic substrates, with the apparent advantages of good yields and excellent enantioselectivities (up to 98% ee) and diastereoselectivities (dr >24:1). A transition-state model has also been proposed to account for the excellent stereocontrol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Air
  • Catalysis
  • Cyclization
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis*
  • Heterocyclic Compounds, 4 or More Rings / chemistry
  • Molecular Structure
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Palladium / chemistry*
  • Stereoisomerism

Substances

  • Heterocyclic Compounds, 4 or More Rings
  • Organometallic Compounds
  • Palladium