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Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles.
- Source :
-
Chemical Communications . 8/11/2017, Vol. 53 Issue 62, p8763-8766. 4p. - Publication Year :
- 2017
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *DERACEMIZATION
*MICHAEL reaction
*STEREOSELECTIVE reactions
Subjects
Details
- Language :
- English
- ISSN :
- 13597345
- Volume :
- 53
- Issue :
- 62
- Database :
- Academic Search Index
- Journal :
- Chemical Communications
- Publication Type :
- Academic Journal
- Accession number :
- 124419416
- Full Text :
- https://doi.org/10.1039/c7cc05164f