Pd/PC-Phos-Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N-Allenamides

Pei-Chao Zhang; Jie Han; Junliang Zhang

doi:10.1002/anie.201904805

Pd/PC-Phos-Catalyzed Enantioselective Intermolecular Denitrogenative Cyclization of Benzotriazoles with Allenes and N-Allenamides

Angew Chem Int Ed Engl. 2019 Aug 12;58(33):11444-11448. doi: 10.1002/anie.201904805. Epub 2019 Jul 4.

Authors

Pei-Chao Zhang¹, Jie Han¹, Junliang Zhang^{1

2}

Affiliations

¹ Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, P. R. China.
² Department of Chemistry, Fudan University, 2005 Songhu Road, Shanghai, 200438, P. R. China.

PMID: 31197921
DOI: 10.1002/anie.201904805

Abstract

Reported herein is an asymmetric Pd/PC-Phos-catalyzed denitrogenative cyclization of benzotriazoles with allenes and N-allenamides, representing the first example of enantioselective denitrogenative cyclizations of benzotriazoles. A series of optically active 3-methyleneindolines were obtained in good yields with high ee values. The use of inexpensive and readily available starting materials, high regio- and enantioselectivity, a broad substrate scope, mild reaction conditions, no need for base, as well as versatile functionalization of the 3-methyleneindolines make this approach attractive.

Keywords: allenamides; allenes; cyclization; heterocycles; palladium.

Publication types

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

Abstract

Publication types

Grants and funding