1996 Fiscal Year Final Research Report Summary
Development of Efficient Chiral Synthetic Process of Bioactive Compounds.
| Project/Area Number |
07557305
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 試験 |
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| Research Field |
医薬分子機能学
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| Research Institution | Kumamoto University |
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Principal Investigator |
KUNIEDA Takehisa Kumamoto University, Pharmceutical Sciences ; Professor., 薬学部, 教授 (80012649)
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| Co-Investigator(Kenkyū-buntansha) |
TAKAMURA Norio Tanabe Pharmaceutical Co.Ltd., Research and Development Section ; Chief, 研究開発部, 部長
ISHIZUKA Tadao Kumamoto University, Pharmaceutical Sciences ; Associate Professor., 薬学部, 助教授 (60176203)
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| Project Period (FY) |
1995 – 1996
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| Keywords | 2-Amino alcohol / 2-Oxazolone / 2-Oxazolidinone / Asymmetric synthesis / Chiral auxiliary / 2-Imidazolone / 2-Imidazolidinone / Chiral synthesis |
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| Research Abstract |
1.Development of Diastereoselective Procedures.
(1) Both enantiomers of sterically congested 2-oxazolidinones and 2-imidazolidinones, which served as efficient chiral auxiliaries, were synthesized by [4+2] cycloaddition of cyclic dienes with 2-oxazolone and 2-imidazolone. The utilities of these auxiliaries in asymmetric synthetic reactions such as alkylations, the Diels-Alder reactions, Michael reactions and aldol reactions were revealed.
(2) The 2-oxazolidinones were hydrolyzed to conformationally fixed 2-amino alcohols of synthetic significance. The lithium salts of N-sulfonyl derivative of amino alcohols thus obtained cleaved meso-dicarboxylic anhydrides to the half esters with almost perfect diastereoselectivity. In contrast, zinc salts reacted with the anhydrides with opposite selectivity.
2.Development of Enantioselective Procedures.
N,N-Dialkylamino alcohols and N-sulfonylamino alcohols which were derived from ringcleavage of the 2-oxazolidinones served as equally effective catalysts in ethylation of aldehydes with ZnEt_2, but interestingly showed completely reversed enantioselectivity.
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Research Products
(20 results)
