2014 Fiscal Year Final Research Report
Aza-spirocyclic synthesis using alkyklation reaction of amines catalyzed by iron catalysts; alkylation reagents derived from esters
| Project/Area Number |
24750043
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
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| Research Institution | Yamaguchi University |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2015-03-31
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| Keywords | アルキル化 / ラジカル反応 / ルテニウム / ヒドロシラン / 銅 |
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| Outline of Final Research Achievements |
In this research, we established new type of alkylation reaction with esters as a alkylating reagents:1)A ruthenium complex, , effectively catalyzes two types of N-alkylation of p-tosylamides by combination of esters (R1CO2R2) as an alkyl source and hydrosilane as the reducing reagents. With primary- and secondary-alkyl esters reductive alkylation occurs to give R3N(CH2R2)Ts. In contrast the reactions with tertiary-alkyl esters result in cleavage of the C-O bond giving rise to introduction of tertiary-alkyl group to form R3N(R2)Ts. These new N-alkylation reactions are useful for construction of natural product skeletons.
2)In the presence of copper complex, alpha-halocarbonyl compounds undergo tert-alkylation of styrene derivatives via radical reaction. A copper catalyst system can induce the alkylation of styrenes with tert-alkyl halides possessing a withdrawing group under very mild conditions. This reaction provides an efficient synthetic methodology for tertiary-alkylated styrenes.
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| Free Research Field |
有機金属
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