Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions

Jean-Nicolas Desrosiers; Liana Hie; Soumik Biswas; Olga V Zatolochnaya; Sonia Rodriguez; Heewon Lee; Nelu Grinberg; Nizar Haddad; Nathan K Yee; Neil K Garg; Chris H Senanayake

doi:10.1002/anie.201606955

Construction of Quaternary Stereocenters by Nickel-Catalyzed Heck Cyclization Reactions

Angew Chem Int Ed Engl. 2016 Sep 19;55(39):11921-4. doi: 10.1002/anie.201606955. Epub 2016 Sep 7.

Affiliations

¹ Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA. [email protected].
² Department of Chemistry and Biochemistry, University of California, Los Angeles, USA.
³ Department of Chemical Development US, Boehringer-Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, Ridgefield, CT, 06877, USA.

PMID: 27600647
DOI: 10.1002/anie.201606955

Abstract

A nickel-catalyzed Heck cyclization for the construction of quaternary stereocenters is reported. This transformation is demonstrated in the synthesis of 3,3-disubstituted oxindoles, which are prevalent motifs seen in numerous biologically active molecules. The method shows broad scope, proceeds in synthetically useful yields, and provides a rare means to construct stereochemically complex frameworks by nonprecious-metal catalysis.

Keywords: Heck reaction; cyclization; heterocycles; homogeneous catalysis; nickel.

Publication types

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