Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 5, Pages 2019-2026Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02848
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Funding
- National Natural Science Foundation of China [21272202, 21572200, J1210042]
- Fundamental Research Funds for the Central Universities
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Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of trifluoromethyl benzoxazinones with pyrroles is reported. Under mild conditions, a range of enantioenriched dihydrobenzoxazinones bearing trifiuoromethylated quaternary stereocenters could be obtained in good to excellent yield and ee. A remarkable fluorine effect is observed, and preliminary mechanistic studies combined with theory calculations suggest that triple-hydrogen-bonding interactions hold the transition structure rigidly and allow the bulky substituents of the catalyst to influence the enantioselectivity.
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