4.2 Article

HIGHLY ACTIVE RHODIUM CATALYST WITH ELECTRON-POOR DIPHOSPHINE ENABLES EFFICIENT SYNTHESIS OF CHIRAL 4-ARYL-delta-LACTONES

Journal

HETEROCYCLES
Volume 80, Issue 1, Pages 157-162

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-09-S(S)40

Keywords

Chiral Lactone; Rhodium Catalyst; Electron-Poor Ligand; Asymmetric 1,4-Addition; Boronic Acid

Funding

  1. Ministry of Education, Culture, Sports, Science and Technology, Japan
  2. JGC-S SCHOLARSHIP FOUNDATION

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Chiral 4-aryl-delta-lactones could be synthesized efficiently with high enantioselectivity through asymmetric 1,4-addition of arylboronic acid to alpha,beta-unsaturated lactones using Rh catalyst including electron-poor diphosphine (MeO-F-12-BIPHEP) at room temperature for 1 h. In particular, our catalytic system proved to be applicable to relatively large coumarin analogues, giving optically pure 4-phenylchroman-2-one analogues in a short time.

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