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Synthesis 2011(21): 3516-3522  
DOI: 10.1055/s-0030-1260209
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Pyrroles in Supercritical Carbon Dioxide: Formal [3+2] Cycloaddition of 2-Benzoyl-Aziridines and Allenoates

Ana L. Cardoso, Rui M. D. Nunes, Luis G. Arnaut, Teresa M. V. D. Pinho e Melo*
Department of Chemistry, University of Coimbra, 3004-535 Coimbra, Portugal
Fax: +351(239)827703; e-Mail: tmelo@ci.uc.pt ;
Further Information

Publication History

Received 8 July 2011
Publication Date:
06 September 2011 (online)

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Abstract

The reactivity of N-benzyl- and N-cyclohexyl-2-benzoyl-3-phenylaziridines toward allenoates in supercritical carbon dioxide (scCO2) is described. The study led to the development of a sustainable and selective approach to pyrrole derivatives and gave a new insight into the mechanism involved in the process.

Key words

cycloaddition - scCO2 - aziridines - allenes - pyrroles

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