Enantioselective Synthesis of Chiral Oxime Ethers: Desymmetrization and Dynamic Kinetic Resolution of Substituted Cyclohexanones

다국어 초록 (Multilingual 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.
Axial‐chirale Cyclohexylidenoxime sind durch katalytische Desymmetrisierung von 4‐substituierten Cyclohexanonen mit O‐Arylhydroxylaminen in Gegenwart eines chiralen Strontium‐BINOL‐Phosphats enantioselektiv zugänglich. Ferner führte die dynamische kinetische Racematspaltung von α‐substituierten Cyclohexanonen in hohen Ausbeuten und Enantioselektivitäten zu vielseitigen Zwischenstufen. M.S.=Molekularsieb.