title: Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones.
abstract: 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.
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE 205A, Tampa, FL, 33620, USA.
authors.forename: Sri Krishna
authors.initials: SK
authors.lastname: Nimmagadda
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, TX, 77843, USA.
authors.forename: Sharath Chandra
authors.initials: SC
authors.lastname: Mallojjala
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE 205A, Tampa, FL, 33620, USA.
authors.forename: Lukasz
authors.initials: L
authors.lastname: Woztas
authors.affiliation: Department of Chemistry, Texas A&M University, College Station, TX, 77843, USA.
authors.forename: Steven E
authors.identifier: 0000-0001-7824-6906
authors.initials: SE
authors.lastname: Wheeler
authors.affiliation: Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE 205A, Tampa, FL, 33620, USA.
authors.forename: Jon C
authors.identifier: 0000-0002-8471-3387
authors.initials: JC
authors.lastname: Antilla
keywords: chirality; enantioelectivity; kinetic resolution; organocatalysis; oximes