期刊
CHEMICAL & PHARMACEUTICAL BULLETIN
卷 66, 期 10, 页码 920-922出版社
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c18-00551
关键词
fluorination; asymmetric catalysis; phase-transfer catalyst; allylic fluoride; chiral tetrasubstituted carbon center
资金
- JSPS [16H05077, 18K06585]
- Basis for Supporting Innovative Drug Discovering and Life Science Research (BINDS) from Japan Agency for Medical Research and Development (AMED)
- Naito Foundation (Japan)
- Research Foundation for Pharmaceutical Sciences
- FUGAKU Trust for Medicinal Research
Asymmetric fluorination of cyclic tetrasubstituted alkenes with a pendant amide group was investigated under dianionic phase-transfer catalysis. Fluorination proceeded with high face selectivity, affording the corresponding allylic fluorides with a chiral tetrasubstituted carbon center with up to 97% enantiomeric excess (ee). It should be noted that deprotonative fluorination occurred mainly in preference to intramolecular nucleophilic attack of the amide group.
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