Issue 62, 2017

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

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

Supplementary files

Article information

Article type
Communication
Submitted
05 Jul 2017
Accepted
12 Jul 2017
First published
12 Jul 2017

Chem. Commun., 2017,53, 8763-8766

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, 53, 8763 DOI: 10.1039/C7CC05164F

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