Synthesis of Optically Pure 2-Azetidinones Having N-Dehydroamino Acid Side-Chains

Benito Alcaide; Concepción Polanco; Miguel A. Sierra

doi:10.1055/s-1998-1667

Synlett 1998; 1998(4): 416-418
DOI: 10.1055/s-1998-1667

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Synthesis of Optically Pure 2-Azetidinones Having N-Dehydroamino Acid Side-Chains

Benito Alcaide^* , Concepción Polanco, Miguel A. Sierra

^*Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense, 28040-Madrid, Spain

Abstract

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An efficient, three step synthesis of optically pure N-vinyl-2-azetidinones 1 starting from α- or β-amino ester imines has been developed. Staudinger reaction between amino ester derived imines and ketene precursors gave 2-azetidinones 2. Enolate formation on the amino ester moiety of the optically pure 2-azetidinones 2, selenylation and, finally, MCPBA treatment afforded N-vinyl-2-azetidinones 1 in good to excellent yields, with total retention of the stereochemistry of the starting material. Compounds 2 bear the functionality needed to place a carboxy group contiguous to the lactam nitrogen, a structural feature common to all the active β-lactam antibiotics.

enantiopure N-vinyl-2-azetidinones - aminoester imines - Staudinger reaction

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