Diastereoselective Synthesis of Dihydro-quinolin-4-ones by a Borane-Catalyzed Redox-Neutral endo-1,7-Hydride Shift
G Wicker, R Schoch, J Paradies - Organic Letters, 2021 - ACS Publications
G Wicker, R Schoch, J Paradies
Organic Letters, 2021•ACS PublicationsThe 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.
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.
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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