期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 80, 期 9, 页码 4797-4802出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00426
关键词
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资金
- Ministry of Education, Culture, Sports, Science and Technology, Japan (MEXT)
- Hoansha Foundation
- MEXT
- MEXT-Supported Program for the Strategic Research Foundation at Private Universities
- Grants-in-Aid for Scientific Research [25460022] Funding Source: KAKEN
A C-amide-substituted O-silylated oxime, (E)-(tert-butyldimethylsiloxyimino)acetic acid N,N-dimethylamide (8b), on treatment with 2.2 equiv of BF3 center dot OEt2, in situ generated boracyclic nitrone-type intermediate BF3 center dot 14, which underwent cycloaddition with alkenes to give 3,5-cis-isoxazolidines as the Major products. The mechanism was strongly supported by isolation of the reaction intermediate 14 that was characterized by X-ray diffraction and its further reaction. This cycloaddition was successfully applied to the synthesis of syn-HPA-12 known as an inhibitor of CERT that mediates the transport of ceramide.
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