Issue 69, 2014
From the journal:

Chemical Communications

A metal-free dyotropic-like rearrangement of 2-oxa allylic alcohols in the presence of organoboronic acids†

Weimin Ye,a   Wenbo Lia  and  Junliang Zhang*a  

* Corresponding authors

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062, P. R. China
E-mail: jlzhang@chem.ecnu.edu.cn

Abstract

The first example of a dyotropic-like rearrangement of 2-oxa allylic alcohols in the presence of catalytic amounts of Selectfluor and DABCO was reported, which provides a facile access to organoboronates. This reaction represents an unprecedented dyotropic rearrangement consisting of cleavage of two vicinal bonds (one C–C bond and one C[double bond, length as m-dash]C bond).

Graphical abstract: A metal-free dyotropic-like rearrangement of 2-oxa allylic alcohols in the presence of organoboronic acids

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Article information

DOI
https://doi.org/10.1039/C4CC03450C
Article type
Communication
Submitted
07 May 2014
Accepted
03 Jul 2014
First published
08 Jul 2014

Chem. Commun., 2014,50, 9879-9882

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A metal-free dyotropic-like rearrangement of 2-oxa allylic alcohols in the presence of organoboronic acids

W. Ye, W. Li and J. Zhang, Chem. Commun., 2014, 50, 9879 DOI: 10.1039/C4CC03450C

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