2011 Fiscal Year Final Research Report
Regio-and Stereoselective Transformation of Internal Allylic Systems
| Project/Area Number |
21350020
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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 |
Organic chemistry
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| Research Institution | Hokkaido University |
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Principal Investigator |
SAWAMURA Masaya 北海道大学, 大学院・理学研究院, 教授 (40202105)
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| Project Period (FY) |
2009 – 2011
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| Keywords | アリル化 / 位置選択性 / パラジウム触媒 / 銅触媒 / 有機ホウ素化合物 / 有機ケイ素化合物 / ヘテロアレーン |
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| Research Abstract |
Transition-metal-catalyzed allylic substitution reactions with nucleophiles are among the most important transformation methods in modern organic synthesis because of their broad substrate scope under mild reaction conditions and applicability to enantioselective reactions, as well as the versatility of the alkene functionality adjacent to the chiral center for stereoselective derivatization. However, allylic substitution of unsymmetrically substituted allylic substrates occurs competitively at the α-and γ-positions due to formation of a (π-allyl)metal intermediate : the regioselectivity is highly dependent on the substitution pattern of the allylic substrates. In this research, the principle of catalytic γ-selective substitution of allylic systems has been established, and new organic synthetic reactions have been developed.
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