Intramolecular reductive ketone–alkynoate coupling reaction promoted by (η2-propene)titanium

Christian Schäfer; Michel Miesch; Laurence Miesch

doi:10.1039/C2OB07049A

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Intramolecular reductive ketone–alkynoate coupling reaction promoted by (η²-propene)titanium†

Christian Schäfer,^a Michel Miesch*^a and Laurence Miesch*^a

Author affiliations

* Corresponding authors

^a Université de Strasbourg, Institut de Chimie, UMR 7177, Laboratoire de Chimie Organique Synthétique, 1 rue Blaise Pascal, BP 296/R8, 67008 Strasbourg-Cedex, France
E-mail: lmiesch@unistra.fr, m.miesch@unistra.fr
Fax: +33 3 68 85 17 54
Tel: +33 3 68 17 51

Abstract

Intramolecular reductive coupling of cycloalkanones tethered to alkynoates in the presence of (η²-propene)titanium was successfully performed to provide hydroxy-esters in a diastereoselective manner. Subsequent lactonization afforded angularly fused unsaturated tricyclic lactones which represent relevant substructures of numerous bioactive compounds.

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Article information

DOI: https://doi.org/10.1039/C2OB07049A
Article type: Paper
Submitted: 07 Dec 2011
Accepted: 07 Feb 2012
First published: 07 Feb 2012

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Org. Biomol. Chem., 2012,10, 3253-3257

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Intramolecular reductive ketone–alkynoate coupling reaction promoted by (η²-propene)titanium

C. Schäfer, M. Miesch and L. Miesch, Org. Biomol. Chem., 2012, 10, 3253 DOI: 10.1039/C2OB07049A

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Organic & Biomolecular Chemistry