Stereoselective synthesis of all-cis boryl tetrahydroquinolines via copper-catalyzed regioselective addition/cyclization of o-aldiminyl cinnamate with B2Pin2

Ya-Ping Bi; He-Min Wang; Hong-Yu Qu; Xian-Chen Liang; Ying Zhou; Xue-Ying Li; Defeng Xu; Mei-Hua Shen; Hua-Dong Xu

doi:10.1039/C8OB03195A

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Stereoselective synthesis of all-cis boryl tetrahydroquinolines via copper-catalyzed regioselective addition/cyclization of o-aldiminyl cinnamate with B₂Pin₂†

Ya-Ping Bi,^a He-Min Wang,^a Hong-Yu Qu,^a Xian-Chen Liang,^a Ying Zhou,^a Xue-Ying Li,^a Defeng Xu,^a Mei-Hua Shen

*^a and Hua-Dong Xu

*^a

Author affiliations

* Corresponding authors

^a Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Pharmaceutical Engineering and Life Science, Changzhou University, Changzhou, Jiangsu Province 213164, China
E-mail: shenmh@cczu.edu.cn, hdxu@cczu.edu.cn

Abstract

A copper catalyzed intramolecular 1,2-carboboration of o-aldiminyl cinnamate has been realized in both regio- and stereoselective fashions. This reaction provides a convenient entry to highly valuable and otherwise challenging cis-2,3,4-trisubstituted tetrahydroquinolines carrying a 4-boryl group. An unusual non-Michael addition intermediate or alternatively, a cyclic enolate is proposed to account for the intriguing all-cis configuration in the final products.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C8OB03195A
Article type: Paper
Submitted: 24 Dec 2018
Accepted: 21 Jan 2019
First published: 23 Jan 2019

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Org. Biomol. Chem., 2019,17, 1542-1546

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Stereoselective synthesis of all-cis boryl tetrahydroquinolines via copper-catalyzed regioselective addition/cyclization of o-aldiminyl cinnamate with B₂Pin₂

Y. Bi, H. Wang, H. Qu, X. Liang, Y. Zhou, X. Li, D. Xu, M. Shen and H. Xu, Org. Biomol. Chem., 2019, 17, 1542 DOI: 10.1039/C8OB03195A

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Organic & Biomolecular Chemistry