Issue 30, 2017
From the journal:

Chemical Communications

Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes†

Zhiwei Jiang,a   Longlei Hou,b   Chunjie Ni,b   Jiangfei Chen,b   Dong Wangb  and  Xiaofeng Tong ORCID logo *ab  

* Corresponding authors

a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai, China

b Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, 1 Gehu Road, Changzhou, China
E-mail: txf@cczu.edu.cn

Abstract

Here, the highly enantioselective construction of 3,3-disubstituted tetrahydropyridines via Pd(0)-catalyzed asymmetric vinylborylation of (Z)-1-iodo-dienes and B2pin2 in the presence of a (S)-p-CF3-BnPHOX ligand is reported. This process is supposed to be initiated by oxidative addition of Pd(0) to vinyl iodide, followed by transmetallation with B2pin2, insertion of the pendant alkene and reductive elimination of alkyl–Pd(II)-Bpin.

Graphical abstract: Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes

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Article information

DOI
https://doi.org/10.1039/C7CC01488K
Article type
Communication
Submitted
27 Feb 2017
Accepted
20 Mar 2017
First published
20 Mar 2017

Chem. Commun., 2017,53, 4270-4273

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Enantioselective construction of quaternary tetrahydropyridines by palladium-catalyzed vinylborylation of alkenes

Z. Jiang, L. Hou, C. Ni, J. Chen, D. Wang and X. Tong, Chem. Commun., 2017, 53, 4270 DOI: 10.1039/C7CC01488K

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