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

Anastasia P. Kadina; Alexander F. Khlebnikov; Mikhail S. Novikov; Pedro J. Pérez; Dmitry S. Yufit

doi:10.1039/C2OB25676B

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Organic & Biomolecular Chemistry

Issue 29, 2012

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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

Anastasia P. Kadina,^a Alexander F. Khlebnikov,*^a Mikhail S. Novikov,^a Pedro J. Pérez^b and Dmitry S. Yufit^c

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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

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

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

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

DOI: 10.1039/C2OB25676B
Received 05 Apr 2012, Accepted 01 Jun 2012
First published online 13 Jun 2012

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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.

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Anastasia P. Kadina
Alexander F. Khlebnikov
Mikhail S. Novikov
Pedro J. Pérez
Dmitry S. Yufit

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Organic & Biomolecular Chemistry

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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Organic & Biomolecular Chemistry

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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