Kinetic resolution of indolines by asymmetric hydroxylamine formation

Gang Wang, Ran Lu, Chuangchuang He and Lei Liu ()
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Gang Wang: Shandong University
Ran Lu: School of Pharmaceutical Sciences
Chuangchuang He: School of Pharmaceutical Sciences
Lei Liu: Shandong University

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Catalytic kinetic resolution of amines represents a longstanding challenge in chemical synthesis. Here, we described a kinetic resolution of secondary amines through oxygenation to produce enantiopure hydroxylamines involving N–O bond formation. The economic and practical titanium-catalyzed asymmetric oxygenation with environmentally benign hydrogen peroxide as oxidant is applicable to a range of racemic indolines with multiple stereocenters and diverse substituent patterns in high efficiency with efficient chemoselectivity and enantio-discrimination. Late-stage asymmetric oxygenation of bioactive molecules that are otherwise difficult to synthesize was also explored.

Date: 2021
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Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-22658-3

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DOI: 10.1038/s41467-021-22658-3

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