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Highly Regio- and Stereoselective Rearrangement of Epoxides to Aldehydes Catalyzed by High-Valent Metalloporphyrin Complex, Cr(TPP)OTf

Kohji Suda,* Taketoshi Kikkawa, Shin-ichiro Nakajima and Toshikatsu Takanami

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan, Email: sudamy-pharm.ac.jp

K. Suda, T. Kikkawa, S.-i. Nakajima, T. Takanami, J. Am. Chem. Soc., 2004, 126, 9554-9555.

DOI: 10.1021/ja047104k (free Supporting Information)


Abstract

Chromium(III) tetraphenylporphyrin triflate is an efficient and characteristic Lewis acid catalyst for a regio- and stereoselective rearrangement of epoxides to aldehydes. Optically active β-siloxy aldehydes are easily available through Sharpless epoxidation of allylic alcohols, followed by silylation and rearrangement.


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Key Words

Rearrangements, Aldehydes


ID: J48-Y2004-1660