Publication | Closed Access
Kinetic Resolution of 1,1′‐Biaryl‐2,2′‐Diols and Amino Alcohols through NHC‐Catalyzed Atroposelective Acylation
84
Citations
63
References
2014
Year
EngineeringKinetic ResolutionChiral AlcoholsAldehyde BackboneEnzyme CatalysisOrganic ChemistryAmino AlcoholsCatalysisNhc‐catalyzed Atroposelective AcylationChemistryMolecular CatalysisAsymmetric CatalysisEnantioselective SynthesisBiomolecular Engineering
Abstract We present here a highly efficient NHC‐catalyzed kinetic resolution of a wide range of 1,1′‐biaryl‐2,2′‐diols and amino alcohols to provide them in uniformly ≥99 % ee . This represents the first highly enantioselective catalytic acylation of axially chiral alcohols. The aldehyde backbone that is incorporated into the chiral acyl azolium intermediate was found to have a significant effect on the enantioselectivity of the process.
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