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

Benjamin H. Rotstein; Andrei K. Yudin

doi:10.1055/s-0030-1260261

Synthesis, Table of Contents

Synthesis 2012; 44(18): 2851-2858
DOI: 10.1055/s-0030-1260261

special topic

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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Abstract

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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.

Key words

aziridines - aldehydes - multicomponent reactions - heterocycles - amphoteric molecules

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References

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