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- Title
Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones.
- Authors
Nimmagadda, Sri Krishna; Mallojjala, Sharath Chandra; Woztas, Lukasz; Wheeler, Steven E.; Antilla, Jon C.
- 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.
- Subjects
CYCLOHEXANONES; OXIMES; STRONTIUM compounds; ORGANIC synthesis; TRANSITION metals; ORGANOCATALYSIS; LIGANDS (Chemistry)
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 9, p2494
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201611602