2012 Fiscal Year Final Research Report
Enantioselective trapping of an α-chiral carbanion next to conjugating electron-withdrawing groups
| Project/Area Number |
23659007
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemical pharmacy
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| Research Institution | Hiroshima University |
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Principal Investigator |
TAKEDA Kei 広島大学, 大学院・医歯薬保健学研究科, 教授 (30135032)
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| Co-Investigator(Kenkyū-buntansha) |
SASAKI Michiko 広島大学, 大学院・医歯薬保健学研究院, 准教授 (30379888)
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| Project Period (FY) |
2011 – 2012
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| Keywords | キラルカルバニオン / 不斉合成 |
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| Research Abstract |
(1) We have demonstrated that a chiral α-nitrile carbanion generated by deprotonation of enantioenriched O-carbamoylcyanohydrin is able to be trapped by a carbon electrophile.
(2) Chirality transfer from an α-silylalcohol to α-carbmoyloxy carbanions was investigated using a Brook rearrangement-mediated SE2’ protonation. Comparison of the extent of the chirality transfer provides a new method for semi-quantitative evaluation of the propensity for racemization of lithiocarbanions next to a conjugative electron -withdrawing group.
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