Ethyl 2-(Diisopropoxyphosphoryl)-2H-azirine-3-carboxylate: Reactions with Nucleophilic
1,3-Dienes

M. José Alves; Américo Lemos; José Enrique Rodriguez-Borges; Xerardo García-Mera; A. Gil Fortes

doi:10.1055/s-0029-1216945

PAPER

Ethyl 2-(Diisopropoxyphosphoryl)-2H-azirine-3-carboxylate: Reactions with Nucleophilic 1,3-Dienes

M. José Alves*^a, Américo Lemos*^b, José Enrique Rodriguez-Borges^c, Xerardo García-Mera^d, A. Gil Fortes^a
^a Departamento de Química, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal
Fax: +351(253)678983; e-Mail: mja@quimica.uminho.pt;
^b Departamento de Química, Bioquímica e Farmácia, Universidade do Algarve, Campus de Gambelas, 8005-137 Faro, Portugal
Fax: +351(289)819403; e-Mail: alemos@ualg.pt;
^c CIQ, Departamento de Química, Faculdade de Ciências, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007 Porto, Portugal
^d Departamento de Química Orgánica, Facultade de Farmacia, Universidade de Santiago de Compostela, 15782 Santiago de Compostela, Spain

Abstract

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Abstract

Ethyl 2-(diisopropoxyphosphoryl)-2H-azirine-3-carboxylate, the first example of an azirine bearing simultaneously ester and phosphonate groups was generated in situ and reacted with a number of 1,3-dienes. Cycloadducts or their ensuing rearranged products were isolated in moderate yields.

Key words

2H-azirines - aza-Diels-Alder cycloaddition - dienophiles - phosphonates

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