1998 Fiscal Year Final Research Report Summary
Research on Asymmetric Reaction with New Chiral Schiff Base-Metal Cpmplexes
| Project/Area Number |
08454202
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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 |
Organic chemistry
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| Research Institution | Yamaguchi University |
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Principal Investigator |
OGUNI Nobuki Yamaguchi University, Faculty of Science, Professor., 理学部, 教授 (60028165)
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| Project Period (FY) |
1996 – 1998
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| Keywords | Asymmetric Catalysis / Optically Active Compounds / Chiral Schiff Base / Titanium Complexes / Asymmetric Silylcyanation / Diketene / ASymmetric Ring-Opening Reaction / Phenyllithium |
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| Research Abstract |
I already invented many new catalytic enantioselective reactions using chiral schiff base-metal complexes as catalyst. One of them was enantioselective addition of trimethylcyanide to aldehydes to give highly optically active cyanohydrins over 90% ee.
The investigations by this project were new some enantioselective catalysis using chiral schiff bases. The first was the enantioselective addition of diketene to aldehydes to give chiral 5-hydroxy-3-ketoesters. Some kind of the products can be applied for the synthesis of new medicine lowering colesteroles in blood. The use of 10 mo1% of chiral titanium catalyst afforded over 90% ee's product in quantitative chemical yield.
The second research was the enantioselective ring opening arylation of symmetrical epoxides such as cyclohexene oxide. Lithium alokoxide of chiral schiff bases in reaction media acts as catalyst to give ring opening product having over 90% ee. The products easily were recrystallized to give optically pure compounds. Also trans-2-arylcyclohexanols are very useful chiral precursors to prepare a variety of medicines. This invension was applied as a patent.
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