Issue 7, 2013
From the journal:

Chemical Communications

Highly regioselective opening of zirconacyclopentadienes by remote coordination: concise synthesis of the furan core of the leupyrrins†

Thomas Debnar,‡a   Sandra Dreisigacker‡a  and  Dirk Menche*b  

* Corresponding authors

a University of Heidelberg, Department of Organic Chemistry, INF 270, D-69120 Heidelberg, Germany, EU

b University of Bonn, Kekulé-Intitute of Organic Chemistry and Biochemistry, Gerhard-Domagk-Str. 1, D-53121 Bonn, Germany, EU
E-mail: dirk.menche@uni-bonn.de
Tel: +49 (0)228-732653

Abstract

An efficient protocol for the highly regioselective opening of aliphatic zirconacyclopentadienes is reported. The one-pot process involves a zirconocene-mediated cyclization of 1,6-diynes and highly selective cleavage of the metallacycles with NBS and enables a concise synthesis of the tetrahydrofuran-core of the leupyrrins.

Graphical abstract: Highly regioselective opening of zirconacyclopentadienes by remote coordination: concise synthesis of the furan core of the leupyrrins

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Article information

DOI
https://doi.org/10.1039/C2CC37678D
Article type
Communication
Submitted
22 Oct 2012
Accepted
29 Nov 2012
First published
30 Nov 2012

Chem. Commun., 2013,49, 725-727

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Highly regioselective opening of zirconacyclopentadienes by remote coordination: concise synthesis of the furan core of the leupyrrins

T. Debnar, S. Dreisigacker and D. Menche, Chem. Commun., 2013, 49, 725 DOI: 10.1039/C2CC37678D

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