The pseudo-multicomponent reaction between propargyl amine, an aldehyde and an electron-deficient alkene is described. The C-H activation takes place thermally and allows to obtain cicloadducts in very good yields and high diastereoselectivities. The relative configuration is determined by X-Ray diffraction analysis of the chiral molecule, obtained as single diastereosiomer, using a chiral maleimide. A brief study of the stability of the possible ylides involved in the process is also mentioned, confirming the high diastereoselectivity observed. The high functional group density of these cycloadducts permits the synthesis of complex heterocycles. After allylation or propargylation of the pyrrolidine nitrogen atom, RCM-DA cycloaddition or a cyclotrimerization with an alkyne are studied, respectively. In this last example, the resulting tetracyclic structures possess potential interest as drugs for the treatment of cystic fibrosis.

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