2016 Fiscal Year Final Research Report
Enantio- and Diastereoselective Cyclopropanation with Halodiazoacetophenone
| Project/Area Number |
26860002
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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 |
Chemical pharmacy
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| Research Institution | Hokkaido University |
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Principal Investigator |
TSUBOWA Koji (竹田幸司) 北海道大学, 薬学研究院, 研究員 (00572497)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | 合成化学 / 不斉触媒反応 / ロジウム(II)錯体 |
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| Outline of Final Research Achievements |
The transition metal-catalyzed asymmetric cyclopropanation reaction of alkenes with diazo compounds represents one of the most powerful means for the construction of optically active cyclopropane building blocks. Hansen and co-workers developed highly diastereoselective cyclopropanations of alkenes with halodiazoacetates, but the asymmetric induction was below 10% ee.
The cyclopropanation with bromodiazoacetophenone under catalysis by Rh2(S-TBPTTL)4 produced cis-cyclopropene product in 75% yield with 85% ee. In addition, it was found that the reaction with chlorodiazoacetophenone afforded the corresponding cyclopropene with 91% ee.
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| Free Research Field |
医歯薬学
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