Highly Enantioselective CuAAC of Functional Tertiary Alcohols Featuring an Ethynyl Group and Their Kinetic Resolution
Kui Liao, Yi Gong, Ren‐Yi Zhu, Cai Wang, Feng Zhou, Jian Zhou
Abstract
-catalyzed azide-alkyne cycloaddition (CuAAC) of tertiary alcohols and their kinetic resolution is reported. This approach allows facile access to multifunctional tertiary alcohols featuring an α-ethynyl or α-triazole moiety, and represents the first successful kinetic resolution of racemates with a tetrasubstituted carbon stereocenter via CuAAC. Newly developed pyridinebisoxazoline (PYBOX) ligands with a C4 phosphonate group play a key role.
Topics & Concepts
StereocenterEnantioselective synthesisKinetic resolutionMoietyCycloadditionChemistryPhosphonateCombinatorial chemistryAzideStereochemistryTertiary alcoholsCatalysisOrganic chemistryClick Chemistry and ApplicationsSynthesis and Catalytic ReactionsCyclopropane Reaction Mechanisms