Stereoselective 1,3-Dipolar Cycloaddition of a Maleate Derivative with Azomethine Ylides Derived from α-Amino Esters: Synthesis of 3-Pyrrolines

• DOI: 10.1055/s-2007-977449
• Publication Date: 2007-05-08T13:28:08Z
• Authors: Sandrine Deloisy; Adrien Soret; Régis Guillot; Gérard Rousseau; Luis Blanco
• Keywords: Dimethyl acetylenedicarboxylate; Azomethine ylide; Derivative (finance)

A new preparation of 3-pyrrolines is described by [3+2] cycloadditions N-metalated azomethine ylides derived from α-amino esters with a dimethyl 7-oxabicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate derivative, followed retro-Diels-Alder reactions. This two-step sequence appears superior to the direct reaction acetylenedicarboxylate and should be applicable solid-phase synthesis.