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Short Paper | Regular issue | Vol 85, No. 12, 2012, pp.3029-3034
Published online, 30th October, 2012
DOI: 10.3987/COM-12-12595
Palladium-Catalyzed Synthesis of a Phosphine Oxide with a Chiral Phosphorus Center via C-H Phosphination

Yoichiro Kuninobu,* Kazuki Origuchi, and Kazuhiko Takai*

*Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan

Abstract

A new phosphine oxide with a chiral phosphine center was synthesized from a bis(biphenyl)phosphine oxide by dehydrogenative intramolecular cyclization via P-H and C-H bond activation under palladium catalysis. The absolute configuration of one enantiomer of the phosphine oxide was determined by single crystal X-ray structure analysis. By reducing the phosphine oxide, the corresponding phosphine, which also has a chiral center, was produced. The phosphine compounds could be optically resolved by chiral HPLC column chromatography.