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Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles

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Abstract

The first catalytic asymmetric dynamic resolution of unprotected racemic 3-(4-alkylcyclohexylidene)indolin-2-ones via a one-step direct vinylogous Michael reaction with chalcones was realized using a chiral N,N′-dioxide/Sc(III) complex catalytic system. A variety of (Z)-4-alkyl-2-((3-oxo-1,3-diarylpropyl)cyclohexylidene)-indolin-2-ones with three stereogenic centers at ξ-, γ- and δ′-positions were obtained in up to 95% yield, 98% ee and 99/1 dr. A possible transition state was proposed to explain the origin of the stereoselectivity.

Graphical abstract: Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles

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Publication details

The article was received on 05 Jul 2017, accepted on 12 Jul 2017 and first published on 12 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC05164F
Citation: Chem. Commun., 2017, Advance Article
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    Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles

    H. Mei, L. Lin, L. Wang, L. Dai, X. Liu and X. Feng, Chem. Commun., 2017, Advance Article , DOI: 10.1039/C7CC05164F

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