Issue 18, 2016
From the journal:

RSC Advances

Highly diastereo-/enantioselective Cu-catalyzed propargylic alkylations of propargyl acetates with cyclic enamines†

Cheng Zhang,ab   Yun-Ze Hui,c   De-Yang Zhangb  and  Xiang-Ping Hu*b  

* Corresponding authors

a Department of Drug Discovery and Biomedical Sciences, South Carolina College of Pharmacy, Medical University of South Carolina, 280 Calhoun Street MSC140 QF307, Charleston, South Carolina 29425, USA

b Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, China
E-mail: xiangping@dicp.ac.cn, xiangping1974@163.com

c Faculty of Engineering and Built Environment, University of Newcastle, Callaghan, NSW 2308, Australia

Abstract

Highly diastereo- and enantioselective copper-catalyzed propargylic alkylations of propargylic acetates with morpholine-derived cyclic enamines for the construction of vicinal tertiary stereocenters have been developed. By the employment of a less sterically hindered chiral tridentate P,N,N-ligand, good to excellent diastereo- (up to >98 : 2 dr) and enantioselectivity (up to 99% ee) could be achieved for a wide range of substrates.

Graphical abstract: Highly diastereo-/enantioselective Cu-catalyzed propargylic alkylations of propargyl acetates with cyclic enamines

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Article information

DOI
https://doi.org/10.1039/C5RA25627E
Article type
Communication
Submitted
02 Tsh 2015
Accepted
26 Phe 2016
First published
28 Phe 2016

RSC Adv., 2016,6, 14763-14767

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Highly diastereo-/enantioselective Cu-catalyzed propargylic alkylations of propargyl acetates with cyclic enamines

C. Zhang, Y. Hui, D. Zhang and X. Hu, RSC Adv., 2016, 6, 14763 DOI: 10.1039/C5RA25627E

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