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Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

ABSTRACT: The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields.

SUBMITTER: Lackner AD

PROVIDER: S-EPMC3827023 | biostudies-literature | 2013 Sep

REPOSITORIES: biostudies-literature

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Single-operation deracemization of 3H-indolines and tetrahydroquinolines enabled by phase separation.

Lackner Aaron D AD Samant Andrew V AV Toste F Dean FD

Journal of the American Chemical Society 20130911 38

The single-operation deracemization of 3H indolines and tetrahydroquinolines is described. An asymmetric redox approach was employed, in which a phosphoric acid catalyst, oxidant, and reductant are present in the reaction mixture. The simultaneous presence of both oxidant and reductant was enabled by phase separation and resulted in the isolation of highly enantioenriched starting materials in high yields. ...[more]

PMID: 24025122

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