1991 Fiscal Year Final Research Report Summary
Highly stereoselective reduction using palladium catalysis and its application to nitrogen containing biologically active substances
| Project/Area Number |
02650634
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Synthetic chemistry
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| Research Institution | Waseda University |
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Principal Investigator |
SHIMIZU Isao Waseda University School of Science and Engineering Associate Professor, 理工学部, 助教授 (50134820)
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| Project Period (FY) |
1990 – 1991
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| Keywords | Palladium Catalyst / Indolizidine Alkaloid / Alkenyl Oxirane / (-)-Nupharamine / Reduction with Formic Acid / (pi-Allyl) palladium Complex |
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| Research Abstract |
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.
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