| Project/Area Number |
03671009
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Tohoku College of Pharmacy |
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Principal Investigator |
HIROI Kunio Tohoku College of Pharmacy, Department of Pharmacy,professor, 薬学部, 教授 (00012641)
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| Co-Investigator(Kenkyū-buntansha) |
FUKUDA Akiko Tohoku college of Pharmacy, Department of Pharmacy, Research Associate, 薬学部, 助手
TAKAKUMA Hisae Tohoku college of Pharmacy, Department of Pharmacy, Research Associate, 薬学部, 助手
ITO Naoko Tohoku college of Pharmacy, Department of pharmacy, Research Associate, 薬学部, 助手
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| Project Period (FY) |
1991 – 1992
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| Project Status |
Completed (Fiscal Year 1992)
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| Budget Amount *help |
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1992: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 1991: ¥1,300,000 (Direct Cost: ¥1,300,000)
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| Keywords | Asymmetric symthesis / Palladium catalyst / pi-Allylpalladium complex / alpha-Amino acid / (S)-Proline / Asymmetric allylation / Asymmetric cyclization / Asymmetric carbon-carbon bond formation / キラルエナミン / リン配位子 |
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| Research Abstract |
We have found the first example of the palladium-catalyzed asymmetric allylations of chiral enamines, imines, and hydrazones derived from readily obtainable optically active alpha-amino acid allyl esters such as (S)-proline and (S)-valine derivatives.
Chiral enamines or hydrazones having phosphine groups, which was derived from (S)-proline derivatives, represented high enantioselectivity in the palladium-catalyzed allylations, in which the phosphine groups served as intramolecular chiral ligands and the great stereoelectronic effects of the anionic counterparts of the allylating reagents on the asymmetric induction were observed.
Chiral enamines bearing allylating parts underwent intramolecular asymmetric allylations under palladium-catalyzed reaction conditions, affording optically active cyclic compounds. this novel method for asymmetric carbon-carbon bond formations was applied to the synthesis of optically active natural products such as indole alkaloids and monoterpenes.
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