期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 81, 期 5, 页码 2019-2026出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b02848
关键词
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资金
- National Natural Science Foundation of China [21272202, 21572200, J1210042]
- Fundamental Research Funds for the Central Universities
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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