DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 1,2-DISUBSTITUTED CYCLOALKANECARBOXALDEHYDES

Article abstract of DOI:10.1016/S0040-4020(01)93269-7

A highly useful method for diastereoselective and enantioselective synthesis of trans- and cis-1,2-disubstituted cycloalkanecarboxaldehydes (trans- and cis-10), useful chiral synthons having asymmetric tertiary and quaternary carbon atoms in vicinal positions in their rings, is devised starting from cycloalkenecarboxaldehydes (5). t-Leucine t-butyl ester (2.R=Bu^t), a highly effective chiral auxiliary reagent in the present method, can be recovered for recycling without any loss of optical purity.Some mechanistic explanations on the strereochemical courses of the reactions are presented.