A palladium-catalyzed enantioselective addition of arylboronic acids to cyclic ketimines

Guoqiang Yang; Wanbin Zhang

doi:10.1002/anie.201302861

A palladium-catalyzed enantioselective addition of arylboronic acids to cyclic ketimines

Angew Chem Int Ed Engl. 2013 Jul 15;52(29):7540-4. doi: 10.1002/anie.201302861. Epub 2013 Jun 10.

Authors

Guoqiang Yang¹, Wanbin Zhang

Affiliation

¹ School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China.

PMID: 23754605
DOI: 10.1002/anie.201302861

Abstract

Sly as Nicox: A palladium-catalyzed addition of arylboronic acids to ketimines has been developed to efficiently provide products in up to 99 % yield and 96 % ee. The reactions could be run under aerobic conditions and with unpurified trifluoroethanol (TFE). A pyrrolidine compound bearing a chiral α-tertiary amine was synthesized in several steps without loss of enantioselectivity. TFA = trifluoroacetate.

Keywords: amines; asymmetric catalysis; enantioselectivity; heterocycles; palladium.