1996 Fiscal Year Final Research Report Summary
Development of the effecient synthetic methods of some pharmeceuticals by using the generalized asymmetric epoxidation
| Project/Area Number |
06558093
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Section | 試験 |
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| Research Field |
Bioorganic chemistry
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| Research Institution | KYUSHU UNIVERSITY |
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Principal Investigator |
KATSUKI Tsutomu Fac.Sci.Dept.Chem.KYUSHU UNIVERSITY,Professor, 理学部, 教授 (40037271)
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| Co-Investigator(Kenkyū-buntansha) |
OHARA Yoshio Nissan Chem.Ind.Ltd.Res, Chairman, 企画研究部, 主査
IRIE Ryo Fac.Sci.Dept.Chem.KYUSHU UNIVERSITY,Res.Associate, 理学部, 助手 (70243889)
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| Project Period (FY) |
1994 – 1996
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| Keywords | asymmetric epoxidation / aziridination / (salen) manganese complex / benzylic hydroxylation / asymmetric oxidation / 不斉酸化 |
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| Research Abstract |
We have studied on asymmetric epoxidation of simple olefins to provide a useful methodology for the synthesis of pharmaceuticals and found that well-designed (salen) manganese (III) complexes are efficient catalysts for epoxidation of conjugated olefins. To develop the more effective catalyst, we examined about the reaction mechanism of epoxidation using a (salen) manganese (III) catalyst this year and could propose a unique mechanism of asymmetric induction by the catalysts : the high asymmetric induction by salen catalyst is mainly attributable to asymmetric non-planar structure of the salen ligand. Based on this new knowledge, we could find that an achiral (salen) manganese (III) complex catalyzes epoxidation in the presence of an optically amine in a enantioselective manner. Although enantioselectivity of the reaction is not high enough for practical use at present, this new methodology using readily available and non-expensive achiral salen catalyst will lead to the development of more economical epoxidation.
We also developed asymmetric aziridination of styrane derivatives and asymmetric benzylic hydroxylation by the modification of the (salen) manganese (III) complex we had reported.
These new reactions are expected to be efficient tools for the synthesis of wide variety of pharmaceuticals.
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