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Paper | Special issue | Vol 77, No. 1, 2009, pp.365-374
Published online, 28th July, 2008
DOI: 10.3987/COM-08-S(F)27
Highly Regioselective Rearrangement of 2,3-Diaryloxiranes into 2,2-Diarylacetaldehydes Catalyzed by Ytterbium Porphyrin Complex Yb(TPP)OTf

Toshikatsu Takanami,* Shin-ichiro Nakajima, Shoichi Nakadai, Fumio Hino, and Kohji Suda*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

[5,10,15,20-Tetraphenylporphynato]ytterbium(III) triflate, Yb(TPP)OTf, is an efficient Lewis acid catalyst for the highly regioselective rearrangement of 2,3-diaryl¬oxiranes into 2,2-diarylacetaldehydes. The catalytic process can be easily performed not only in dichloroethane but also in a more environmentally friendly solvent, benzotrifluoride.