期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 140, 期 8, 页码 2785-2788出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b13690
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资金
- JSPS [16H05077]
- Basis for Supporting Innovative Drug Discovering and Life Science Research (BINDS) from ANIED
- Naito Foundation (Japan)
- Research Foundation for Pharmaceutical Sciences
- FUGAKU Trust for Medicinal Research
- Grants-in-Aid for Scientific Research [16H05077] Funding Source: KAKEN
Inspired by the dicationic nature of the electrophilic fluorinating reagent, Selectfluor (1), we rationally designed a series of dicarboxylic acid precatalysts (2), which, when deprotonated, act as anionic phase transfer catalysts for asymmetric fluorination of alkenes. Among them, 2a having the shortest linker moiety efficiently catalyzed unprecedented 6-endo-fluoro-cyclization of various allylic amides, affording fluorinated dihydrooxazine compounds with high enantioselectivity (up to 99% ee). In addition to cyclic substrates, acyclic trisubstituted alkenes underwent the reaction with good diastereoselectivity, whereas low diastereoselectivity was observed for linear disubstituted alkenes. Results suggest that the reaction proceeds via a fluoro-carbocation intermediate.
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