Studies on the titanium-catalyzed cyclopropanation of nitriles.

Org Biomol Chem

UMR 6519--Réactions Sélectives et Applications, CNRS-Université de Reims Champagne-Ardenne, BP 1039, 51687 REIMS Cedex 2, France.

Published: October 2005

AI Article Synopsis

  • * Cyanoesters yielded spirocyclopropanelactams, while cyanocarbonates produced either spirocyclopropane oxazolidinones or aminocyclopropylcarbinols.
  • * The research highlights a brief synthesis of a naturally occurring compound, aminocyclopropanecarboxylic acid, showcasing the practicality of the introduced methodology.

Article 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(O(i)Pr)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.

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Source
http://dx.doi.org/10.1039/b508367bDOI Listing

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