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Communication | Special issue | Vol 80, No. 1, 2010, pp.157-162
Published online, 18th August, 2009
DOI: 10.3987/COM-09-S(S)40
■ Highly Active Rhodium Catalyst with Electron-Poor Diphosphine Enables Efficient Synthesis of Chiral 4-Aryl-δ-lactones

Toshinobu Korenaga,* Ryota Maenishi, Kazutaka Osaki, and Takashi Sakai*

*Department of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 1-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

Chiral 4-aryl-δ-lactones could be synthesized efficiently with high enantioselectivity through asymmetric 1,4-addition of arylboronic acid to α,β-unsaturated lactones using Rh catalyst including electron-poor diphosphine (MeO-F12-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.