Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines

Liyin Jiang; Peng Cao; Min Wang; Bin Chen; Bing Wang; Jian Liao

doi:10.1002/anie.201607493

Highly Diastereo- and Enantioselective Cu-Catalyzed Borylative Coupling of 1,3-Dienes and Aldimines

Angew Chem Int Ed Engl. 2016 Oct 24;55(44):13854-13858. doi: 10.1002/anie.201607493. Epub 2016 Sep 29.

Authors

Liyin Jiang^{1

2}, Peng Cao^{3

4}, Min Wang^{1

2}, Bin Chen⁵, Bing Wang^{1

2}, Jian Liao^{6

7

8}

Affiliations

¹ Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041, China.
² University of Chinese Academy of Sciences, Beijing, 100049, China.
³ Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041, China. caopeng@cib.ac.cn.
⁴ University of Chinese Academy of Sciences, Beijing, 100049, China. caopeng@cib.ac.cn.
⁵ College of Chemical Engineering, Sichuan University, Chengdu, 610065, China.
⁶ Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu, 610041, China. jliao@cib.ac.cn.
⁷ University of Chinese Academy of Sciences, Beijing, 100049, China. jliao@cib.ac.cn.
⁸ College of Chemical Engineering, Sichuan University, Chengdu, 610065, China. jliao@cib.ac.cn.

PMID: 27682640
DOI: 10.1002/anie.201607493

Abstract

A Cu-catalyzed diastereo- and enantioselective borylative coupling reaction of 1,3-dienes with imines was realized. Branched homoallylic amines are readily prepared in a syn-selective manner with high regio-, diastereo- and enantioselectivity. Moreover, these three-component coupling reactions feature good functional-group compatibility and easy access to the substrates and catalyst.

Keywords: 1,3-dienes; asymmetric catalysis; borylative coupling; copper; imines.

Publication types

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