Highly regio- and stereoselective rearrangement of epoxides to aldehydes catalyzed by high-valent metalloporphyrin complex, Cr(TPP)OTf.
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 beta-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.
Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan. suda@my-pharm.ac.jp
Kohji
K
Suda
Taketoshi
T
Kikkawa
Shin-Ichiro
S
Nakajima
Toshikatsu
T
Takanami