Asymmetric Hydrogenation of Racemic Allylic Alcohols via an Isomerization–Dynamic Kinetic Resolution Cascade
Kun Wang, Saisai Niu, Xin Guo, Weijun Tang, Dong Xue, Jianliang Xiao, Huaming Sun, Chao Wang
Abstract
Prochiral racemic allylic alcohols are converted to enantioenriched chiral alcohols bearing adjacent stereocenters catalyzed by a diamine diphosphine Ru complex in the presence of tBuOK. The protocol features a broad substrate scope (56 examples) and high diastereo- and enantioselectivities (up to >99:1 dr, >99% ee) and could be applied to the synthesis of enantioenriched chromane and indane compounds. Mechanistic studies suggest that the reaction proceeds via tBuOK-promoted allylic alcohol isomerization followed by Ru-catalyzed hydrogenative dynamic kinetic resolution.
Topics & Concepts
ChemistryKinetic resolutionAllylic rearrangementIsomerizationStereocenterCatalysisIndaneEnantioselective synthesisCascade reactionOrganic chemistryAsymmetric Hydrogenation and CatalysisCatalysis for Biomass ConversionSurface Chemistry and Catalysis