Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles?
Chemical Communications Pub Date: 2017-07-12 DOI: 10.1039/C7CC05164F
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.
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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