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Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones
Author(s) -
Nimmagadda Sri Krishna,
Mallojjala Sharath Chandra,
Woztas Lukasz,
Wheeler Steven E.,
Antilla Jon C.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611602
Subject(s) - desymmetrization , enantioselective synthesis , kinetic resolution , oxime , chemistry , organic chemistry , stereochemistry , catalysis
Axially chiral cyclohexylidene oxime ethers exhibit unique chirality because of the restricted rotation of C=N. The first catalytic enantioselective synthesis of novel axially chiral cyclohexylidene oximes has been developed by catalytic desymmetrization of 4‐substituted cyclohexanones with O‐arylhydroxylamines and is catalyzed by a chiral BINOL‐derived strontium phosphate with excellent yields and good enantioselectivities. In addition, chiral BINOL‐derived phosphoric acid catalyzed dynamic kinetic resolution of α‐substituted cyclohexanones has been performed and yields versatile intermediates in high yields and enantioselectivities.