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Aza‐Michael Reactions of Isatin Imines: Deeper Insight and Origin of the Stereoselectivity
Author(s) -
Metsala Andrus,
Žari Sergei,
Kanger Tõnis
Publication year - 2016
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201600584
Subject(s) - isatin , chemistry , imine , stereoselectivity , thiourea , michael reaction , catalysis , ring (chemistry) , selectivity , hydrogen atom , sulfur , hydrogen bond , computational chemistry , medicinal chemistry , organic chemistry , molecule , alkyl
Abstract An asymmetric organocatalytic aza‐Michael reaction of imines derived from isatin with unsaturated 1,4‐dicarbonyl compounds was investigated by means of DFT calculations. It was found that, in addition to the activation of the reactants by hydrogen bonds, several π–π interactions were responsible for the high enantioselectivity of the reaction. In the computationally proposed transition state model, an interaction of the sulfur atom of the thiourea catalyst and aromatic π‐electron system of the phenyl ring of imine occurred, providing high selectivity.