Stereoselective cyclization of silylated epoxy aldehydes into piperidines. Effect of the silicon group

What is it about?

A series of 2- or 3-silyl-epoxy aldehydes derivatives bearing a glycinyl sidechain have been prepared and tested in intramolecular aldolization. Highly stereoselective cyclization occurs and provides the N-heterocycle framework which is useful for the synthesis of polyhydroxylated piperidines. The presence of the silicon group on the epoxy moiety strongly influenced the stereochemical outcome of the reaction. Silicon atom; aldolization; palladium catalysis; amination; piperidines

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