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

Xiang-Yu Chen; Sun Li; Qiang Liu; Mukesh Kumar; Anssi Peuronen; Kari Rissanen; Dieter Enders

doi:10.1002/chem.201802420

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

Chemistry. 2018 Jul 11;24(39):9735-9738. doi: 10.1002/chem.201802420. Epub 2018 Jun 25.

Authors

Xiang-Yu Chen¹, Sun Li¹, Qiang Liu¹, Mukesh Kumar¹, Anssi Peuronen², Kari Rissanen², Dieter Enders¹

Affiliations

¹ Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074, Aachen, Germany.
² Department of Chemistry, Nanoscience Center, University of Jyvaskyla, 40014, JYU, Finland.

PMID: 29847691
DOI: 10.1002/chem.201802420

Abstract

A highly efficient strategy for the kinetic resolution of Michael adducts was realized using a chiral N-heterocyclic carbene catalyst. The kinetic resolution provides a new convenient route to single diastereomers of cyclohexenes and Michael adducts in good yields with high enantiomeric excesses (up to 99 % ee with a selectivity factor of up to 458). This "two flies with one swat" concept allows the synthesis of these two synthetically valuable compound classes at the same time by a single transformation.

Keywords: Michael adducts; N-heterocyclic carbenes; asymmetric synthesis; cyclohexenes; kinetic resolution.