| Project/Area Number |
07457614
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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 | 一般 |
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| Research Field |
Chemical pharmacy
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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) |
MATSUNAGA Hirohumi Kumamoto University, Pharmaceutical Sciences ; Assistant., 薬学部, 助手 (10274713)
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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| Project Status |
Completed (Fiscal Year 1996)
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| Budget Amount *help |
¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1996: ¥2,200,000 (Direct Cost: ¥2,200,000)
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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.Chiral 2-Oxazolidinones and 2-Imidazolidinones Auxiliaries.
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.Conformationally Fixed 2-Amino Alcohols.
The 2-oxazolidinones, mentioned above, were hydrolyzed to conformationally fixed 2-amino alcohols of synthetic significance.
(1) N,N-Dialkylamino alcohols and N-sulfonylamino alcohols served as equally effective catalysts in ethylation of aldehydes with ZnEt_2, but showed completely reversed enantioselectivity.
(2) Lithium salts of N-sulfonylamino alcohols cleaved meso-dicarboxylic anhydrides to the half esters with almost perfect diastereoselectivity. In contrast, zinc salts reacted with the anhydrides with opposite selectivity.
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