| Co-Investigator(Kenkyū-buntansha) |
KANAI Motomu The University of Tokyo, Graduate School of Pharmaceutical Sciences, Associate Professor (20243264)
MATSUNAGA Shigeki The University of Tokyo, Graduate School of Pharmaceutical Sciences, Assistant Professor (50334339)
KUMAGAI Naoya The University of Tokyo, Graduate School of Pharmaceutical Sciences, Assistant Professor (40431887)
SOHTOME Yoshihiro The University of Tokyo, Graduate School of Pharmaceutical Sciences, Assitant Professor (50431888)
OHSHIMA Takashi The University of Tokyo, Graduate School of Pharmaceutical Sciences, Assitant Professor (10313123)
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| Budget Amount *help |
¥453,700,000 (Direct Cost: ¥349,000,000、Indirect Cost: ¥104,700,000)
Fiscal Year 2007: ¥81,900,000 (Direct Cost: ¥63,000,000、Indirect Cost: ¥18,900,000)
Fiscal Year 2006: ¥81,900,000 (Direct Cost: ¥63,000,000、Indirect Cost: ¥18,900,000)
Fiscal Year 2005: ¥81,900,000 (Direct Cost: ¥63,000,000、Indirect Cost: ¥18,900,000)
Fiscal Year 2004: ¥81,900,000 (Direct Cost: ¥63,000,000、Indirect Cost: ¥18,900,000)
Fiscal Year 2003: ¥126,100,000 (Direct Cost: ¥97,000,000、Indirect Cost: ¥29,100,000)
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| Research Abstract |
We developed a practical catalytic asymmetric Strecker reaction of ketimines using glucose-derived ligands. Directing toward industrial application, we improved the catalyst turnover efficiency in 100 times using an achiral protic additive. Inexpensive HCN can be used as a cyanide source in this reaction. This is the most general and practical catalytic asymmetric Strecker reacton of ketimines to date. In addition, we developed a new efficient synthetic route of the chiral ligand, which allowed us to synthesize both enantiomers of the ligand. The related catalyst can promote highly enantioselective ring-opening reaction of meso-aziridines with TMSN_3. This reaction was a platform for the synthesis of anti-influenza drug, Tamiflu.
Et_2Zn/linked-BINOL catalyst promoted both anti-and syn-selective direct Mannich reaction of hydroxy ketones. Both diastereomers of the products can be synthesized depening on the reaction conditions with up to 99% ee. The catalyst loading was reduced to 0.01 mol %, which is the far lowest catalyst loading in asymmetric Mannich reaction. The same catalyst also promoted aldol reaction and Michael reaction using the minimum amount of the catalyst.
A chiral rare earth metal-amide catalyst was recently developed, and found to be effective in asymmetric animation reactions. This finding led to develop a practical synthetic route of ranirestat, an anti-diabetic agent.
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