Issue 16, 2000
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones

Giorgio Adembri,a   Gianluca Giorgi,b   Raffaella L. Lampariello,a   Maria L. Paolia  and  Alessandro Sega*a  

* Corresponding authors

a Istituto di Chimica Organica, Via Aldo Moro, Siena, Italy
E-mail: sega@unisi.it
Fax: +39-0577-234278

b Centro Interdipartimentale di Analisi e Determinazioni Strutturali, Via Aldo Moro, Siena, Italy

Abstract

The behaviour of 4-hydroxy-4-methylcyclopent-2-enone and related 4-substituted cyclopent-2-enones towards 1,3-dipolar cycloaddition with nitrile oxides is studied. The reactions are always completely regioselective while the diastereofacial selectivity depends on the nature of the substituents. Remarkably, the reaction of 4-acetoxycyclopent-2-enone shows complete regio- and diastereo-facial selectivity.

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Article information

DOI
https://doi.org/10.1039/B003549L
Article type
Paper
Submitted
03 May 2000
Accepted
29 Jun 2000
First published
04 Aug 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 2649-2656

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Regio- and diastereo-selectivity in 1,3-dipolar cycloadditions of nitrile oxides to 4-substituted cyclopent-2-enones

G. Adembri, G. Giorgi, R. L. Lampariello, M. L. Paoli and A. Sega, J. Chem. Soc., Perkin Trans. 1, 2000, 2649 DOI: 10.1039/B003549L

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