1997 Fiscal Year Final Research Report Summary
Development of versatile synthetic route for 1,2-diamines as excellent chiral auxiliary.
| Project/Area Number |
08672431
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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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 |
ISHIZUKA Tadao Kumamoto University, Pharmaceutical Sciences ; Associate Professor., 薬学部, 助教授 (60176203)
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| Project Period (FY) |
1996 – 1997
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| Keywords | 2-Imidazolone / 2-Imidazolidinone / 1,2-Diamine / Optical resolution / Chiral auxiliary / Chiral synthesis |
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| Research Abstract |
1.Versatile Syunthetic Route for 1,2-Diamines from 2-Imidazolone.
2-Imidazolone was proved to be a excellent building block for the synthesis of 1,2-diamines. Wide variety of trans-4,5-disubstituted 2-imidazolidinones could by synthesized by an addition reaction of Br_2 to the olefinic moiety of the 2-imidazolone and subsequent substitution reactions. Hydorlytic conversion to 1,2-diamines also succeeded.
2.Conformationally Fixed 2-Imidazolidinones as Chiral Auxiliaries.
Both enantiomers of sterically congested 2-imidazolidinones, which served as efficient chiral auxiliaries, were synthesized by [4+2] cycloaddition of cyclic dienes with 2-imidazolone. The utilities of these auxiliaries in asymmetric synthetic reactions such as alkylations, the Diels-Alder reactions and aldol ractions were revealed.
3.Conversion of 1,2-Diamines to 2-Imidazolines.
2-Imidazolines were synthesized by dehydration reactions of the amide derivatives of the 1,2-diamines by phosphorus oxychloride. Further applications as chiral ligands are now in progress.
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