Journal
ACS CATALYSIS
Volume 9, Issue 10, Pages 9599-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b03567
Keywords
photoredox catalysis; aerobic; alkene difunctionalization; isoxazolidines; glycines
Categories
Funding
- NSFC [21672052]
- Henan Province [14IRTSTHN006, 152300410057, 15A150006, 182102310246]
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An access to isoxazolidines featuring visible-light induced aerobic difunctionalization of alkenes is reported. alpha-Amino radicals generated via oxidative decarboxylation of N-aryl glycines are added to alkenes and the resulting radical intermediates are trapped by superoxides. The peroxides undergo swift intramolecular amine oxidation to provide the valuable isoxazolidines. Alkenes with varied functionalization can be applied. The isoxazolidine ring can be readily opened via reduction by zinc in acetic acid to afford gamma-lactams in high yield.
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