Issue 31, 2020, Issue in Progress

Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction

Abstract

A novel class of chiral N,N,N imine-containing ligands derived from TsDPEN (N-(p-tosyl)-1,2-diphenylethylene-1,2-diamine) has been developed and applied to the copper-catalyzed asymmetric Kinugasa reaction. The copper(II) salt proved to be an efficient catalyst precursor, and it provides an efficient way to synthesize enantioenriched cis-β-lactam. The pathway is air-tolerant and easily manipulated, and the ligands are easy to synthesize. A working model is proposed in which the stereocontrolling step is the [2 + 2] cycloaddition between ketene and imine to explain the observed stereoselectivities.

Graphical abstract: Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction

Supplementary files

Article information

Article type
Paper
Submitted
12 Apr 2020
Accepted
04 May 2020
First published
12 May 2020
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2020,10, 18107-18114

Development of TsDPEN based imine-containing ligands for the copper-catalysed asymmetric Kinugasa reaction

C. Xu, Y. Yang, Y. Wu, F. He, H. He, P. Deng and H. Zhou, RSC Adv., 2020, 10, 18107 DOI: 10.1039/D0RA03276J

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