Issue 29, 2012
From the journal:

Organic & Biomolecular Chemistry

Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to estercarbonyl – experimental and DFT computational study†

Anastasia P. Kadina,a   Alexander F. Khlebnikov,*a   Mikhail S. Novikov,a   Pedro J. Pérezb  and  Dmitry S. Yufitc  

* Corresponding authors

a Department of Chemistry, Saint Petersburg State University, Universitetskii pr. 26, 198504 St. Petersburg, Russia
E-mail: alexander.khlebnikov@pobox.spbu.ru
Fax: +7 812 4286939
Tel: +7 812 4284021

b Laboratorio de Catálisis Homogénea, Departamento de Química y Ciencias de los Materiales, Unidad Asociada al CSIC, Centro de Investigación en Química Sostenible (CIQSO), Universidad de Huelva, Campus de El Carmen s/n, 21007 Huelva, Spain
E-mail: perez@dqcm.uhu.es
Fax: +34 959219942
Tel: +34 959 219956

c Department of Chemistry, University of Durham, Durham, South Road, UK
E-mail: d.s.yufit@durham.ac.uk
Fax: +44 191-334-2051
Tel: +44 191-334-2004

Abstract

Intramolecular 1,3-dipolar cycloaddition of alkoxycarbonyl-substituted azomethine ylides to ester carbonyl was realized for the first time in the reaction of imines of O-acylsalicylic aldehyde with ethyl diazoacetate in the presence of Cu(tfacac)2. The stereoselectivity of the cycloaddition is explained using DFT calculations.

Graphical abstract: Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl – experimental and DFT computational study

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Article information

DOI
https://doi.org/10.1039/C2OB25676B
Article type
Paper
Submitted
05 Apr 2012
Accepted
01 Jun 2012
First published
13 Jun 2012

Org. Biomol. Chem., 2012,10, 5582-5591

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Intramolecular cycloaddition of azomethine ylides, from imines of O-acylsalicylic aldehyde and ethyl diazoacetate, to ester carbonyl – experimental and DFT computational study

A. P. Kadina, A. F. Khlebnikov, M. S. Novikov, P. J. Pérez and D. S. Yufit, Org. Biomol. Chem., 2012, 10, 5582 DOI: 10.1039/C2OB25676B

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