Issue 44, 2013
From the journal:

Organic & Biomolecular Chemistry

Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones†

Aaron Christopher,a   Dahniel Brandes,a   Stephen Kellya  and  Thomas G. Minehan*a  

* Corresponding authors

a Department of Chemistry and Biochemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, CA 91330, USA
E-mail: thomas.minehan@csun.edu
Fax: +1 818 677 4062
Tel: +1 818 677 3315

Abstract

Treatment of allyl-1,1-dichlorovinyl ethers with n-BuLi at −78 °C, followed by quenching with ketones, epoxides, and oxetanes, leads to highly substituted β-, γ-, and δ-lactones in good to excellent yields.

Graphical abstract: Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C3OB41777H
Article type
Communication
Submitted
31 Aug 2013
Accepted
01 Oct 2013
First published
01 Oct 2013

Org. Biomol. Chem., 2013,11, 7658-7661

Permissions

Request permissions

Low temperature n-butyllithium-induced [3,3]-sigmatropic rearrangement/electrophile trapping reactions of allyl-1,1-dichlorovinyl ethers. Synthesis of β-, γ- and δ-lactones

A. Christopher, D. Brandes, S. Kelly and T. G. Minehan, Org. Biomol. Chem., 2013, 11, 7658 DOI: 10.1039/C3OB41777H

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements