Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori-Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

J Org Chem. 2021 Mar 19;86(6):4849-4858. doi: 10.1021/acs.joc.0c02981. Epub 2021 Mar 8.

Abstract

3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr's and er's up to 99:1 via a C═C and C═O one-pot reduction in the presence of 2-5 mol % Noyori-Ikariya-type RuII chiral complexes and HCO2Na as a hydrogen source under asymmetric transfer hydrogenation-dynamic kinetic resolution (ATH-DKR) conditions. The oxidation of theses substrates resulted in the enantioselective synthesis of the natural homoisoflavanone dihydrobonducellin and its carba-analogues.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hydrogenation
  • Kinetics
  • Stereoisomerism
  • Tetralones*

Substances

  • Tetralones