2017 Fiscal Year Final Research Report
Inversions in asymmetric conjugate addition reaction of cyclic enones catalyzed by the Cu/NHC-AgX system
| Project/Area Number |
26410127
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Kansai University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2018-03-31
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| Keywords | 不斉触媒反応 / カルベン配位子 / 共役付加反応 / 銅触媒反応 / 金属錯体 / 錯体触媒 / 立体反転 / アート錯体 |
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| Outline of Final Research Achievements |
We reported that the chiral (CH2)2-bridged azolium salt bearing hydroxy-amide group or the corresponding N-heterocyclic carbene (NHC)-Ag complex promoted the Cu-catalyzed asymmetric conjugate addition reaction.
Interestingly, the reversal of enantioselectivity was achieved by changing the order of addition of starting materials. When dialkyl zinc was added to THF solution containing CuOTf, NHC-Ag complex (or azolium salt) and enone, the reaction produced the corresponding 1,4-adduct (Method A).
In contrast, the enantioselectivity of the 1,4-addition reaction was reversed when enone was added to the mixture of a Cu(I) salt, NHC-Ag complex and dialkyl zinc (Method B).
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| Free Research Field |
有機合成化学
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