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Kinetic Resolution of a Planar‐Chiral [2.2]Paracyclophane Derivative by Helical‐Peptide‐Catalyzed Michael Addition of Nitromethane
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.201500594
Subject(s) - nitromethane , chemistry , michael reaction , planar chirality , enantioselective synthesis , kinetic resolution , enantiomer , adduct , substituent , peptide , stereochemistry , chirality (physics) , derivative (finance) , enone , catalysis , organic chemistry , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , financial economics , economics
A resin‐supported peptide catalyst was developed for kinetic resolution of a planar‐chiral [2.2]paracyclophane derivative through Michael addition of nitromethane to an enone substituent on the paracyclophane structure. A helix‐based peptide was effective to discriminate the planar chirality of the [2.2]paracyclophane structure, and to convert one enantiomer preferentially into the Michael adduct. By optimizing the peptide sequence at the N‐terminus of the helical chain, highly enantioselective resolution was attained.