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Chem Pharm Bull (Tokyo). 2018;66(10):920-922. doi: 10.1248/cpb.c18-00551.

Asymmetric Fluorination of Cyclic Tetrasubstituted Alkenes with a Pendant Amide Groups under Dianionic Phase-Transfer Catalysis.

Author information

1
School of Pharmaceutical Sciences, University of Shizuoka.

Abstract

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.

KEYWORDS:

allylic fluoride; asymmetric catalysis; chiral tetrasubstituted carbon center; fluorination; phase-transfer catalyst

PMID:
30270238
DOI:
10.1248/cpb.c18-00551
[Indexed for MEDLINE]
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