期刊
ORGANIC LETTERS
卷 23, 期 9, 页码 3626-3630出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01018
关键词
-
资金
- German Science Foundation (DFG) [PA 1562/16-1]
The borane-catalyzed synthesis of dihydroquinoline-4-ones has been developed, with high yields and excellent diastereoselectivity. The reaction mechanism is investigated through kinetic, isotope labeling, and computational experiments.
The borane-catalyzed synthesis of dihydroquinoline-4-ones is developed. The amino-substituted chalcones undergo a 1,7-hydride shift upon Lewis acid activation to form a zwitterionic iminium enolate, which collapses to the dihydroquinoline-4-one scaffold. The reaction proceeds in high yields (75-99%) with an excellent diastereoselectivity of up to >99:1 (cis:trans). The reaction mechanism is investigated by kinetic, isotope labeling, and computational experiments.
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