Highly stereoselective reduction using palladium catalysis and its application to nitrogen containing biologically active substances

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We have developed useful a synthetic method for preparation of nitrogen containing organic compounds using a palladium-catalyzed reaction as a key reaction. Thus, reaction of optically active alkenyl oxiranes and formic acid in the presence of a catalytic amount of palladium-phosphine complexes gives the optically active homoallylic alcohols, whose hydroxy group is substituted with a nitrogen atom selectively to give optically active amines. The delta-amino ketons or delta-amino esters obtained are cyclized to optically active piperidine or indolizidine compounds. Chiral synthesis (-)-nupharamine and the dendrobatid alkaloids 205A, 209B, and 235B were carried out from these compounds.