PRODUCTION OF ADJACENTLY SUBSTITUTED KETONES

摘要

PURPOSE:To obtain the titled compound having various kind of organic groups introduced at alpha position and beta position and useful as medicine, agricultural chemical and perfume or intermediates thereof in high yield, by reacting a alpha,beta-unsaturated carbonyl compound with an organic copper compound and then reacting the resultant product with aldehydes. CONSTITUTION:Cyclopentenones expressed by formula I (Q is H or protected OH; R2' and R4' are H or lower alkyl) is reacted with a compound expressed by the formula RACu (RA is 1-20C alkyl or alkenyl capable of having protected OH) in an aprotonic inert organic medium in the presence of a trihydrocarbon phosphine (preferably tri-n-butylphosphine) preferably at -40--78 deg.C and the resultant product is reacted with a compound expressed by the Rc CHO (Rc is H or 1-20C hydrocarbon group capable of having protected OH or carboxyl) in the presence of a Lewis acid at ambient temperature - -78 deg.C to provide the aimed compound.