Development of highly efficient asymmetric synthesis process directed for "racemic switch" of the racemic medicines
| Project/Area Number |
16590084
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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 |
Drug development chemistry
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| Research Institution | Sojo University |
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Principal Investigator |
KUNIEDA Takehisa Sojo Univ., Faculty of Pharmaceutical Sciences, Professor, 薬学部, 教授 (80012649)
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| Co-Investigator(Kenkyū-buntansha) |
MATSUNAGA Hirofumi Kumamoto Univ., Graduate School of Medical and Pharmaceutical Sciences, Research Associate, 大学院・医学薬学研究部, 助手 (10274713)
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| Project Period (FY) |
2004 – 2005
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| Project Status |
Completed (Fiscal Year 2005)
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| Budget Amount *help |
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2005: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2004: ¥2,100,000 (Direct Cost: ¥2,100,000)
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| Keywords | 2-Oxazolidinone / 2-Imidazolidinone / 2-Thiazolidinone / Kinetic resolution / Asymmetric alkylation / Asymmetric transfer hydrogenation / Asymmetric Diels-Alder reaction / Catalytic dissymmetrization / 屋根付き / 不斉合成 / 1,2-ジアミン / 水素移動型不斉還元反応 / イミノチオエーテル / 2-チアゾリン / 不斉補助剤 / 不斉配位子 / ラセミックスイッチ / キラル合成子 / 触媒的不斉化 / 不斉アルキル化反応 |
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| Research Abstract |
The aim of this research is to establish the methodology for i) simple preparation of tricyclic "roofed" 2-oxazolidinones, 2-imidazolidinones and 2-thiazolidinones with conformational rigidity and steric congestion as extremely powerful chiral auxiliaries by catalytic resolution, and ii) excellent asymmetric reactions with bicyclic 2-amino alcohols, 1,2-diamines and 2-aminothiols derived from the above tricyclic compounds and their derivatives, directed for "racemic switch" of the racemic medicines.
1.Easy access to highly efficient chiral auxiliaries by kinetic resolution
The optically active "roofed" 2-oxazolidinones, 2-imidazolidinones and 2-thiazolidinones were readily obtained from kinetic resolution with oxazaborolidine catalysts.
2.Application of highly efficient chiral "roofed" ligands
Bicyclic "roofed" 2-amino alcohols, 1,2-diamines and 2-aminothiols derived from the corresponding tricyclic compounds have been proven to be good to excellent chiral ligands for following metal-catalyzed asymmetric reactions :
(1)Asymmetric borane reduction of ketones with oxazaborolidine-borane system ("2-Aminoalcohol" ligands).
(2)Practical synthesis of versatile chiral synthons, 4,5-dialkoxy-2-imidazolidinone ("2-Aminoalcohol" ligands).
(3)Ruthenium (II)-catalyzed asymmetric transfer hydrogenation of ketones ("cis-1,2-Diamine" ligands).
(4)Pd (II)-catalyzed asymmetric alkylation of allylacetates ("2-Aminothiol" ligands).
(5)Cu (II)-catalyzed asymmetric Diels-Alder reaction ("2-Aminothiol" ligands).
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Report
(3 results)
Research Products
(25 results)
