1996 Fiscal Year Final Research Report Summary
Construction of Asymmetric Space
| Project/Area Number |
05234104
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| Research Category |
Grant-in-Aid for Scientific Research on Priority Areas
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| Allocation Type | Single-year Grants |
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| Research Institution | The University of Tokyo |
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Principal Investigator |
KOGA Kenji University of Tokyo, Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (10012600)
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| Co-Investigator(Kenkyū-buntansha) |
NAKAMURA Eiichi University of Tokyo, Graduate School of Science, Professor, 大学院・理学系研究科, 教授 (00134809)
TOMIOKA Kiyoshi Osaka University, Institute of Scientific and Industrial Research, Professor, 産業科学研究所, 教授 (50114575)
MUKAIYAMA Teruaki Science University of Tokyo, Faculty of Science, Professor, 理学部, 教授 (60016003)
FUJI Kaoru Kyoto University, Institute of Chemical Research, Professor, 化学研究所, 教授 (20027056)
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| Project Period (FY) |
1993 – 1995
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| Keywords | asymmetric space / chiral lithium amide / asymmetric deprotonation / asymmetric alkylation / asymmetric protonation / chiral memory / asymmetric addition / stereoselective glycosidation |
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| Research Abstract |
"Construction of Asymmetric Space" plays a central role in asymmetric synthesis. Investigations have been made on the construction of efficient asymmetric spaces and its applications to design novel methods of asymmetric synthesis and catalytic asymmetric synthesis. Following results were obtained.
1) Multidentate chiral lithium amides and chiral amines that can form efficient chiral spaces by chelation were designed and synthesized. Novel asymmetric reactions, such as asymmetric deprotonation, alkylation, and protonation, were developed using these chiral bases. These asymmetric reactions were further developed to catalytic asymmetric reacation. 2) Evidences for the existence of chiral enolates from optically active alpha-amino acid derivatives by deprotonation were found. The new concept "Chiral Memory" was developed and applied to the synthsis of optically active compounds. 3) To utilize sugar derivatives as useful compounds having efficient chiral spaces, highly stereoselective glycosidation methods giving the product in high yields were developed. 4) Chiral di-ethers and amodophosphine derivatives providing efficient chiral spaces were designed and synthesized. They were proved to be useful for the catalytic asymmetric conjugate addition reactions of organolithium and organocopper reagents. 5) Experimental ant theoretical studies were made on the nature of asymmetric spaces for the purpose to deisgn novel asymmetric synthesis. Highly stereoselective addition reactions were developed using novel organocopper reagents and allylzinc complexes.
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