Studies on the reaction of acyl phosphonates with aldehydes in the presence of proline

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2009
Yalçınkaya, Hatice
Acyl phosphonates are interesting precursors for the synthesis of biologically active compounds. In the first part, the acyl phosphonates are synthesized starting from the corresponding acyl chloride. The acyl chlorides are converted into acyl phosphonates by using trialkylphosphites. The reaction of acyl phosphonates with aldehydes in the presence of proline furnished not the suggested aldol products via proline catalyzed aldol reaction but bicyclic products via one pot tricomponent 1,3-dipolar cycloaddition reaction. The formation of the bicyclic compound was suggested as followed; The formation of iminium salt of proline with aldehyde followed by decarboxylation furnished azomethine. The 1,3-dipolar cycloaddition of the formed azomethine with carbonyl group of acyl phosphonate afforded substituted hexahydro pyrrolo oxazole structures. 1,3-Dipolar cycloaddition forms the basis of the most preparatively useful procedures for the synthesis of five-membered heterocycles. One example is the 1,3-dipolar cycloaddition of azomethine ylides (from imines) and alkenes, which allows the stereoselective synthesis of pyrrolidines or proline derivatives.

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Citation Formats
H. Yalçınkaya, “Studies on the reaction of acyl phosphonates with aldehydes in the presence of proline,” M.S. - Master of Science, Middle East Technical University, 2009.