2010 Fiscal Year Final Research Report
Search for carbon-carbon bond formation by the use of boranonitrone
| Project/Area Number |
20790018
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Single-year Grants |
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| Research Field |
Chemical pharmacy
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| Research Institution | Showa Pharmaceutical University |
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Principal Investigator |
MORITA Nobuyoshi Showa Pharmaceutical University, 薬学部, 講師 (00433847)
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| Project Period (FY) |
2008 – 2010
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| Keywords | 有機化学 |
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| Research Abstract |
Boranonitrone, generated from protected oxime with BF_3.OE_t2, underwent intermolecular cycloaddition with alkenes to afford the corresponding isoxazolidines in good yields. Interestingly, the cycloaddition of N-borano-C-ethoxycarbonyl nitrone with alkenes gave 3,5-trans-isoxazolidines, whereas the reaction of tent-butyldimethylsilyloximino-N,N-dimethylethane-amide with alkenes afforded 3,5-cis-isoxazolidines. This reaction is very useful for synthesis of 1,3-anti and 1,3-syn aminoalcohols by reductive cleavage of an N-O bond. Additionally, the reaction of N-borano-C-ethoxycarbonyl nitrone with carbon radical species afforded the corresponding hydroxylamines in good yields.
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