Desymmetrization of <i>gem</i>-diols <i>via</i> water-assisted organocatalytic enantio- and diastereoselective cycloetherification
Ryuichi Murata, Akira Matsumoto, Keisuke Asano, Seijiro Matsubara
Abstract
The first desymmetrization of gem-diols forming chiral hemiketal carbons was accomplished via organocatalytic enantio- and diastereoselective cycloetherification, which afforded optically active tetrahydropyrans containing a chiral hemiketal carbon and tetrasubstituted stereocenters bearing synthetically versatile fluorinated groups. The desymmetrization of silanediols was also demonstrated as an asymmetric route to chiral silicon centers.
Topics & Concepts
DesymmetrizationChemistryOrganocatalysisOrganic chemistryStereochemistryCombinatorial chemistryCatalysisEnantioselective synthesisAsymmetric Synthesis and CatalysisAnalytical Chemistry and ChromatographyAxial and Atropisomeric Chirality Synthesis