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Desymmetrization of Prochiral Cyclopentenes Enabled by Enantioselective Palladium-Catalyzed Oxidative Heck Reaction

Guihua Chen, Jian Cao, Qian Wang and Jieping Zhu*

*Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015 Lausanne, Switzerland, Email:

G. Chen, J. Cao, Q. Wang, J. Zhu, Org. Lett., 2020, 22, 322-325.

DOI: 10.1021/acs.orglett.9b04357


In the presence of a catalytic amount of Pd(TFA)2 and a chiral Pyox ligand, an oxidative Heck reaction between arylboronic acids and 4-substituted or 4,4-disubstituted cyclopent-1-enes provides arylated products with concurrent creation of two stereocenters in good yields with excellent diastereo- and enantioselectivities under an atmosphere of oxygen.

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Key Words

Cyclopentenes, Oxygen

ID: J54-Y2020