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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 8
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Original Articles

Remarkable Stereocontrol in 1,3-Dipolar Cycloaddition of Acyclic Nitrones: Investigation of the Cycloaddition of C,N-Diaryl Nitrones to Methyl Cinnamate Under Different Reaction Conditions

Pizush Kanti Biswas Centre of Advanced Studies on Natural Products Including Organic Synthesis, Department of Chemistry, Calcutta University, Kolkata, India
,
Debasish Bandyopadhyay Centre of Advanced Studies on Natural Products Including Organic Synthesis, Department of Chemistry, Calcutta University, Kolkata, India
,
Thierry Prangé LCRB, UMR 8015–Université Paris Descartes–CNRS, Faculté de Pharmacie, Paris, France
,
Alain Neuman LCRB, UMR 8015–Université Paris Descartes–CNRS, Faculté de Pharmacie, Paris, France
&
Avijit Banerji Centre of Advanced Studies on Natural Products Including Organic Synthesis, Department of Chemistry, Calcutta University, Kolkata, IndiaCorrespondence[email protected]
Pages 1146-1159 | Received 28 Dec 2009, Published online: 21 Mar 2011
 
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Abstract

Investigation of the cycloaddition of C,N-diarylnitrones to methyl cinnamate under different reaction conditions were carried out. Two diastereoisomeric and one regioisomeric cycloadducts were isolated and characterized by spectroscopic and x-ray data. Remarkable change in selectivity was noticed in solvent-free condition and in the presence of ytterbium triflate as catalyst.

ACKNOWLEDGMENT

The authors thank the Indian Council for Cultural Relations (ICCR) for financial assistance to P. K. Biswas (present address: BCSIR Laboratory, Dhanmondi, Dhaka-1205, Bangladesh).

Notes

Present affiliation for Debasish Bandyopadhyay: Department of Chemistry, University of Texas–Pan American, Edinburg, Texas, USA.

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