Flexible access to 2,3,5,6-tetrasubstituted dehydropiperidines by Ni- or Co-catalyzed site-selective cross-coupling using Vilsmeier-Haack-derived α-chloro-β-formyltetrahydropyridines

Document Type

Article

Department or Administrative Unit

Chemistry

Publication Date

9-19-2018

Abstract

A flexible and cost-effective method for the highly functional group-compatible and site-selective cross-coupling of readily affordable α-chloro-β-formyltetrahydropyridines has been developed, under nickel or cobalt catalysis, leading to the rapid synthesis of 2,3,5,6-tetrasubstituted dehydropiperidines bearing α-amino allylic stereocenters. Cobalt-catalyzed reductive cross-coupling of chloro enaminals with electronically-diverse bromostyrenes as coupling partners proceeds in good yields and with high E/Z selectivity to afford Diels-Alder-suitable cross-conjugated 1,3-dienes.

Comments

This article was originally published in Tetrahedron Letters. The full-text article from the publisher can be found here.

Due to copyright restrictions, this article is not available for free download from ScholarWorks @ CWU.

Journal

Tetrahedron Letters

Rights

© 2018 Elsevier Ltd. All rights reserved.

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