Highly regio-, diastereo- and enantioselective deracemization of axially chiral 3-alkylideneoxindoles.
Chem Commun (Camb)
; 53(62): 8763-8766, 2017 Aug 11.
Article
em En
| MEDLINE
| ID: mdl-28730202
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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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Idioma:
En
Revista:
Chem Commun (Camb)
Ano de publicação:
2017
Tipo de documento:
Article