Copper-catalyzed ring-opening C(sp3)-N coupling of cycloketone oxime esters: access to 1°, 2° and 3° alkyl amines

Li Tian; Shuangqiu Gao; Rui Wang; Yang Li; Chunlin Tang; Lili Shi; Junkai Fu

doi:10.1039/c9cc02030f

Copper-catalyzed ring-opening C(sp³)-N coupling of cycloketone oxime esters: access to 1°, 2° and 3° alkyl amines

Chem Commun (Camb). 2019 May 10;55(37):5347-5350. doi: 10.1039/c9cc02030f. Epub 2019 Apr 17.

Authors

Li Tian¹, Shuangqiu Gao¹, Rui Wang¹, Yang Li¹, Chunlin Tang¹, Lili Shi², Junkai Fu³

Affiliations

¹ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China. fujk109@nenu.edu.cn.
² Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China. shill@pkusz.edu.cn.
³ Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun 130024, China. fujk109@nenu.edu.cn and Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China. shill@pkusz.edu.cn.

PMID: 30994128
DOI: 10.1039/c9cc02030f

Abstract

A novel copper-catalyzed C(sp³)-N coupling of cycloketone oxime esters with nitrogen nucleophiles has been realized. All of the N-aryl/alkylanilines, anilines and benzophenone imine could be employed in this protocol to produce a variety of 1°, 2° and 3° alkyl amines in one or two steps. These resultant cyano-containing alkyl amines were proven to be versatile synthetic building blocks in a variety of chemical transformations.