Journal
ORGANIC LETTERS
Volume 23, Issue 18, Pages 7112-7117Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c02510
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Funding
- National Natural Science Foundation of China [21871228]
- Natural Science Foundation of Yunnan Province [2018FY001015]
- Scientific Research Foundation of Education Department of Yunnan Province [2021Y033]
- Program for Changjiang Scholars and Innovative Research Team in University [IRT_17R94]
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A photochemical protocol is developed for the synthesis of chiral 3-hydroxyoxindoles by coupling diarylamines and alpha-ketoesters using tandem photoredox and chiral phosphoric acid catalysis. The chiral phosphoric acid plays a crucial role in controlling the stereochemistry of the downstream radical-radical cross-coupling process.
A photochemical protocol that couples diarylamines and alpha-ketoesters to afford the chiral 3-hydroxyoxindoles through tandem photoredox and chiral phosphoric acid catalysis is developed. The reaction involves an enantioselective photochemical radical-radical cross-coupling process. The chiral phosphoric acid is discovered to play crucial roles by decreasing the reductive potentials of alpha-ketoesters and stereocontrolling the downstream asymmetric radical-radical cross-coupling via the formation of pentacoordinate complex.
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