Synthesis 2012; 44(18): 2851-2858
DOI: 10.1055/s-0030-1260261
special topic
© Georg Thieme Verlag Stuttgart · New York

Aziridine-2-carboxaldehyde Dimers Undergo Homo-Ugi 4-Component-5-center Reactions

Benjamin H. Rotstein
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: +1(416)9467676   eMail: ayudin@chem.utoronto.ca
,
Andrei K. Yudin*
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON, M5S 3H6, Canada, Fax: +1(416)9467676   eMail: ayudin@chem.utoronto.ca
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Publikationsverlauf

Received: 18. April 2012

Accepted: 11. Mai 2012

Publikationsdatum:
11. Juli 2012 (online)

Abstract

Dimeric α-aziridine aldehydes have been used as the aldehyde component in Ugi and Passerini reactions. The highly reactive mixed anhydride intermediate is subject to nucleophilic attack by the aziridine, leading to ‘homo-Ugi’ β-acylaziridinyl-α-aminoamides. The products can be readily transformed into substituted lactones.

 
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