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

Thomas Debnar; Sandra Dreisigacker; Dirk Menche

doi:10.1039/C2CC37678D

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Chemical Communications

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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

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

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

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

DOI: 10.1039/C2CC37678D
Received 22 Oct 2012, Accepted 29 Nov 2012
First published online 30 Nov 2012

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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.

Abstract from Methods in Organic Synthesis 2013

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

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

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