Synthesis of 1,3-disubstituted cyclohexenes from dienylethers via sequential hydrozirconation/deoxygenative cyclisation

Amandine Payet; Benjamin Blondeau; Jean-Bernard Behr; Jean-Luc Vasse

doi:10.1039/C8OB02925C

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Synthesis of 1,3-disubstituted cyclohexenes from dienylethers via sequential hydrozirconation/deoxygenative cyclisation†

Amandine Payet,^a Benjamin Blondeau,^a Jean-Bernard Behr

^a and Jean-Luc Vasse

*^a

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* Corresponding authors

^a Institut de Chimie Moléculaire de Reims, CNRS (UMR 7312) and Université de Reims Champagne Ardenne, 51687 Reims Cedex 2, France
E-mail: jean-luc.vasse@univ-reims.fr

Abstract

Access to 1,3-disubstituted cyclohexenes from zirconocenes containing a latent electrophilic allylic fragment is described. Requiring a specific conformation, 6-endo-trig cyclisation is based on the TMSOTf-mediated generation of a stabilized carbocation.

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

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Article information

DOI: https://doi.org/10.1039/C8OB02925C
Article type: Communication
Submitted: 23 Nov 2018
Accepted: 22 Dec 2018
First published: 26 Dec 2018

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Org. Biomol. Chem., 2019,17, 798-802

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Synthesis of 1,3-disubstituted cyclohexenes from dienylethers via sequential hydrozirconation/deoxygenative cyclisation

A. Payet, B. Blondeau, J. Behr and J. Vasse, Org. Biomol. Chem., 2019, 17, 798 DOI: 10.1039/C8OB02925C

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Organic & Biomolecular Chemistry

Synthesis of 1,3-disubstituted cyclohexenes from dienylethers via sequential hydrozirconation/deoxygenative cyclisation†

Abstract

Supplementary files

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Synthesis of 1,3-disubstituted cyclohexenes from dienylethers via sequential hydrozirconation/deoxygenative cyclisation

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