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Cover Picture: Palladium–N‐Heterocyclic Carbene (NHC)‐Catalyzed Asymmetric Synthesis of Indolines through Regiodivergent C(sp 3 )H Activation: Scope and DFT Study (Chem. Eur. J. 46/2014)
Author(s) -
Katayev Dmitry,
Larionov Evgeny,
Nakanishi Masafumi,
Besnard Céline,
Kündig E. Peter
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201490190
Subject(s) - enantiopure drug , chemistry , enantiomer , carbene , racemic mixture , stereochemistry , catalysis , methylene , palladium , medicinal chemistry , enantioselective synthesis , organic chemistry
A rare, perfect case of a highly selective regiodivergent reaction of a racemic mixture is presented. Upon interaction with the Pd–( S,S )‐NHC catalyst (NHC=N‐heterocyclic carbene), the R enantiomer takes the right fork and the S enantiomer the left one. Thus, the racemic mixture reacts to give two regioisomeric enantiopure products. In this reaction a methyl CH activation competes with an asymmetric CH‐bond activation in a methylene unit to give single enantiomers of substituted indolines. DFT was the tool to map out the course of the reaction and to extend and rationalize the outcome. For more details see the Full Paper by E. P. Kündig et al. on page 15021 ff.