2009 Fiscal Year Final Research Report
Stereocontrol of Chiral Carbanions in Tandem Reactions
| Project/Area Number |
19390006
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Hiroshima University |
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Principal Investigator |
TAKEDA Kei Hiroshima University, 大学院・医歯薬学総合研究科, 教授 (30135032)
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| Co-Investigator(Kenkyū-buntansha) |
SASAKI Michiko 広島大学, 大学院・医歯薬学総合研究科, 助教 (30379888)
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| Project Period (FY) |
2007 – 2009
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| Keywords | 不斉転写 / キラルカルバニオン / [2,3]-Wittig転位 / 不斉反応 / 転位反応 |
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| Research Abstract |
(1) We have found that the extent of chirality transfer in [2,3]-Wittig rearrangement employing a chiral β-substituted allyl benzyl carbanion can be used as a tool for evalulation of the effect of substituents on the configurational stability of a chiral carbanion through a double bond.
(2) Treatment of (R, Z)-3-(tert-butyldimethylsilyl)-1-cyano-3-hydroxyprop-1-enyl carbamate with a catalytic amount of a base afforded (S, E)-3-(tert-butyldimethylsilyloxy)-1-cyanoallyl diisopropyl- carbamate, showing that S_E2'-type reaction of allylsilicates proceeds in an anti-mode fashion. The overall process is equivalent to trapping of an enantioenriched C-chiral carbanion at α-position of nitrile group in up to 77% ee.
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