Multicomponent silver-catalyzed 1,3-dipolar cycloadditions using ethyl glyoxylate and 2,2-dimethoxyacetaldehyde azomethine ylides

JOSÉ M. SANSANO-GIL; JUAN MANCEBO ARACIL; CARMEN NÁJERA; ALBERTO CAYUELAS

Congreso; VII International School on Organometallic Chemistry Marcial Moreno Mañas; 2014

Multicomponent reactions, and particularly cycloaddition,have very interesting perspectives and applications because do not waste atoms during their whole processes. 1,3-dipolar cycloaddition involving metallo-azomethine and electrophilic alkenes are good examples from this typeof transformation but are no so frequently described. Firstly, the1,3-metallodipole precursor can be obtained in situ by imine formation from the corresponding aldehyde and alfa-amino ester. Second, the metal catalyst wouldfix the geometry of the metallodipole favouring a high stereocontrol during the dipolarophile approach and operates under milder conditions. Polysubstituted pyrrolidines or proline derivatives usually with an aromatic or heteroaromating at 5-position can be prepared. In this communication, the silver mediated multicomponent 1,3-DC between alfa amino esters, dipolarophiles and functionalized aldehydes such as ethyl glyoxylate and 2,2-dimethoxyacetaldehydewill be considered.