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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted
Sri Krishna Nimmagadda1, Sharath Chandra Mallojjala2, Lukasz Woztas1
1Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, CHE 205A, Tampa, FL, 33620, USA.
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.
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