Kinetic Resolution of Acyclic Tertiary Propargylic Alcohols by NHC-Catalyzed Enantioselective Acylation
Hao An, Shifei Liu, Shaojie Wang, Xiaoyi Yu, Chenqi Shi, Haonan Lin, Si Bei Poh, Hui Yang, Ming Wah Wong, Yu Zhao, Zhifeng Tu, Shenci Lu
Abstract
We report herein an efficient NHC-catalyzed kinetic resolution of acyclic tertiary propargylic alcohols that provides them in high to excellent enantioselectivity. This is the first example of kinetic resolution realized by enantioselective acylation. The recovered enantioenriched alcohols can be facilely converted into other valuable compounds such as densely functionalized tertiary alcohols and carbmates in high yields and excellent stereopurity. Density functional theory calculations were performed to determine the reaction mechanism and to understand the origin of enantiodiscrimination.
Topics & Concepts
Kinetic resolutionEnantioselective synthesisChemistryAcylationTertiary alcoholsCatalysisOrganic chemistryResolution (logic)Combinatorial chemistryArtificial intelligenceComputer scienceN-Heterocyclic Carbenes in Organic and Inorganic ChemistryCatalytic Cross-Coupling ReactionsCatalytic C–H Functionalization Methods