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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| Project Status |
Completed (Fiscal Year 2010)
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| Budget Amount *help |
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2010: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2009: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2008: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
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| Keywords | 有機化学 / ボラノニトロン / イソキサゾリジン / 1,3-anti-アミノアルコール / 1,3-syn-アミノアルコール / NH-ニトロン / 分子内オキシム-オレフィン環化付加反応 / イソキゾリジン / 分子内オキシムーオレフィン環化付加反応 / N-ボラノニトロン / 1, 3-anti-アミノアルコール / オキシム |
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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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Report
(4 results)
Research Products
(23 results)
