Enantioselective Intramolecular Copper-Catalyzed Borylacylation

Andrew Whyte; Katherine I Burton; Jingli Zhang; Mark Lautens

doi:10.1002/anie.201808460

Enantioselective Intramolecular Copper-Catalyzed Borylacylation

Angew Chem Int Ed Engl. 2018 Oct 15;57(42):13927-13930. doi: 10.1002/anie.201808460. Epub 2018 Sep 21.

Authors

Andrew Whyte¹, Katherine I Burton¹, Jingli Zhang^{1

2}, Mark Lautens¹

Affiliations

¹ Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, M5S 3H6, Canada.
² School of Chemistry, Chemical Engineering and Life Sciences, Wuhan University of Technology, 122 Luoshi Road, Wuhan, 430074, China.

PMID: 30160825
DOI: 10.1002/anie.201808460

Abstract

An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon-boron bond provides a platform for a wide array of diversification.

Keywords: asymmetric catalysis; boron; copper; cyclizations; heterocycles.

Publication types

Research Support, Non-U.S. Gov't