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Kinetic Resolution of a Planar‐Chiral [2.2]Paracyclophane Derivative by Helical‐Peptide‐Catalyzed Michael Addition of Nitromethane (Eur. J. Org. Chem. 23/2015)
Author(s) -
Akagawa Kengo,
Nishi Nobuhiro,
Yoshikawa Isao,
Kudo Kazuaki
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201590064
Subject(s) - chemistry , nitromethane , planar chirality , moiety , michael reaction , enantiomer , substituent , kinetic resolution , stereochemistry , cyclophane , molecule , chirality (physics) , peptide , derivative (finance) , enantioselective synthesis , catalysis , organic chemistry , financial economics , economics , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
The cover picture shows the kinetic resolution of a racemic mixture of a [2.2]paracyclophane derivative with planar chirality. A helix‐based peptide catalyst was effective to convert one enantiomer (purple molecule) preferentially over the other (green molecule). The N‐terminal primary amino group of the peptide activates the enone substituent of the cyclophane compound, and Michael addition of nitromethane takes place. Although the planar‐chiral [2.2]paracyclophane moiety is somewhat distant from the carbonyl group, highly selective resolution was attained by the helical peptide that can provide a suitable reaction site. Details are discussed in the article by K. Kudo et al. on 5055 ff .