Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes

Tuo Jiang; Teresa Bartholomeyzik; Javier Mazuela; Jochen Willersinn; Jan-E Bäckvall

doi:10.1002/anie.201501048

Palladium(II)/Brønsted Acid-Catalyzed Enantioselective Oxidative Carbocyclization-Borylation of Enallenes

Angew Chem Int Ed Engl. 2015 May 11;54(20):6024-7. doi: 10.1002/anie.201501048. Epub 2015 Mar 24.

Authors

Tuo Jiang¹, Teresa Bartholomeyzik, Javier Mazuela, Jochen Willersinn, Jan-E Bäckvall

Affiliation

¹ Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm SE-10691 (Sweden).

Abstract

An enantioselective oxidative carbocyclization-borylation of enallenes that is catalyzed by palladium(II) and a Brønsted acid was developed. Biphenol-type chiral phosphoric acids were superior co-catalysts for inducing the enantioselective cyclization. A number of chiral borylated carbocycles were synthesized in high enantiomeric excess.

Keywords: carbocyclization; chiral anion; chiral phosphoric acid; oxidation; palladium.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution Non-Commercial NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.