On the diastereoselectivity of the 1,2-reduction of 2-alkyl-4-hydroxycyclopentenones with sodium borohydride in the presence of cerium (III): Synthesis of prostaglandin precursors

Abstract

During studies related to the elaboration of prostaglandin precursors we have reduced the ketonic carbonyl group of a number of optically active 2-substituted-4-hydroxy-2-cyclopentenone esters and ethers using sodium borohydride and cerium trichloride under various conditions. High diastereoselectivity is achieved only with some 4-substituents.