Issue 19, 2005
From the journal:

Organic & Biomolecular Chemistry

Studies on the titanium-catalyzed cyclopropanation of nitriles

Christophe Laroche,a   Dominique Harakat,a   Philippe Bertus*a  and  Jan Szymoniak*a  

* Corresponding authors

a UMR 6519 – Réactions Sélectives et Applications, CNRS-Université de Reims Champagne-Ardenne, BP 1039, 51687 REIMS Cedex 2, France
E-mail: philippe.bertus@univ-reims.fr, jan.szymoniak@univ-reims.fr
Fax: 00 33 326 913 166
Tel: 00 33 326 913 244

Abstract

The Ti-mediated reaction of Grignard reagents with nitriles was investigated with sub-stoichiometric amounts of titanium isopropoxide. Cyanoesters were converted to spirocyclopropanelactams in good yields using as low as 0.05 eq of Ti(OiPr)4. Under similar conditions, cyanocarbonates led to spirocyclopropane oxazolidinones and/or aminocyclopropylcarbinols. A very short synthesis of the naturally occurring aminocyclopropanecarboxylic acid illustrates the usefulness of this methodology.

Graphical abstract: Studies on the titanium-catalyzed cyclopropanation of nitriles

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Article information

DOI
https://doi.org/10.1039/B508367B
Article type
Paper
Submitted
14 Jun 2005
Accepted
26 Jul 2005
First published
23 Aug 2005

Org. Biomol. Chem., 2005,3, 3482-3487

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Studies on the titanium-catalyzed cyclopropanation of nitriles

C. Laroche, D. Harakat, P. Bertus and J. Szymoniak, Org. Biomol. Chem., 2005, 3, 3482 DOI: 10.1039/B508367B

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