2012 Fiscal Year Final Research Report
Catalytic Asymmetric Synthesis of Cage-type Organic Compounds by New Stereo-controlled Approach
| Project/Area Number |
23655091
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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 |
Synthetic chemistry
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| Research Institution | Waseda University |
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Principal Investigator |
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| Project Period (FY) |
2011 – 2012
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| Keywords | 面不斉 / 大環状化合物 / カゴ型化合物 / 不斉認識 / 不斉触媒 |
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| Research Abstract |
I reported an enantioselective ortho-lithiation of achiral paracyclophanes with oxygen atoms as directed moieties at both ends of ansa-chain using a chiral lithium reagent. The reaction of an unflippable 1,n-dioxa[n]paracyclophane (n?□11) with sec- utyllithium and (-)-sparteine gave the chiral mono-lithiated product. Additional amount of sec-butyllithium gave C_2-symmetric dilithiated product. The quenching of these lithium salts by appropriate electrophiles gave various planar-chiral aracyclophanes with excellent ee. The planar-chiral mono- and diphosphines, which were prepared by the above protocols, were used as chiral ligands in transition metal-catalyzed reactions.
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