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
J. Am. Chem. Soc., 2004, 126 (31), pp 9554–9555
DOI: 10.1021/ja047104k
Publication Date (Web): July 20, 2004
Copyright © 2004 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, suda@my-pharm.ac.jp

Abstract

Abstract Image

Chromium(III) tetraphenylporphyrin triflate, Cr(TPP)OTf, works as an efficient and characteristic Lewis acid catalyst in the regio- and stereoselective rearrangement of epoxides to aldehydes. This Cr(TPP)OTf-catalyzed reaction is an operationally simple and especially convenient method for synthesizing optically active β-siloxy aldehydes from 2,3-epoxy silyl ethers which are readily available in enantiomerically enriched forms by the Sharpless epoxidation of allylic alcohols followed by silylation.

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History

  • Published In Issue August 11, 2004
  • Received May 17, 2004

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