Host: Division of Organic Chemistry, The Pharmaceutical Society of Japan
Pages 98-99
Catalytic and regio- and stereoselective rearrangement of epoxides to aldehydes via an alkyl migration can easily be achieved with a high valent metalloporphyrin complex, Cr(tpp)OTf, at a low catalyst loading (1–20 mol%). The yield and regio- and stereoselectivity of the catalytic process are generally good to high, and almost fully comparable to those of the corresponding reactions done stoichiometrically in a bulky organoaluminum reagent MABR. Since we have previously reported that Fe(tpp)X (X = OTf or ClO4) catalyzes the rearrangement of epoxides to ketones via a hydrogen mygration, ketones and aldehydes can selectively be prepared from epoxides in a highly controlled manner by the simple choice of Fe(III) and Cr(III) as a central metal ion of the porphyrin catalysts.
