6533b82efe1ef96bd1293ca9

RESEARCH PRODUCT

Highly Enantioselective Kinetic Resolution of Michael Adducts through N-Heterocyclic Carbene Catalysis: An Efficient Asymmetric Route to Cyclohexenes

Xiang-yu ChenDieter EndersQiang LiuAnssi PeuronenSun LiKari RissanenMukesh Kumar

subject

Cyclohexenesasymmetric synthesis010402 general chemistry01 natural sciencesCatalysisCatalysisKinetic resolutionMichael adductschemistry.chemical_compoundkinetic resolutionN-heterocyclic carbenesta116orgaaniset yhdisteetkemiallinen synteesi010405 organic chemistryOrganic ChemistryDiastereomerEnantioselective synthesisGeneral ChemistryCombinatorial chemistry0104 chemical scienceschemistrycyclohexenesEnantiomerSelectivityCarbene

description

Ahighly efficient strategy for the kinetic resolu-tion of Michael adductswas realized using achiral N-het-erocyclic carbene catalyst.The kinetic resolution providesanew convenientroute to single diastereomers of cyclo-hexenes and Michael adducts in good yields with highenantiomeric excesses (up to 99 % ee with aselectivityfactor of up to 458). This “two flies with one swat” con-cept allows the synthesis of these two synthetically valua-ble compound classes at the same time by asingle trans-formation. peerReviewed

https://doi.org/10.1002/chem.201802420