Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant?

Chemical Communications Pub Date: 2015-04-03 DOI: 10.1039/C5CC02176F

Abstract

Palladium/chiral diphosphine-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a terminal reductant affords cis-disubstituted pyrrolidine, tetrahydrofuran, and spiro carbocycle in high enantioselectivity. The formate does not cause allylpalladium reduction under the catalysis. The highly stereoselective cyclization would proceed through a cationic η1-allylpalladium ligated by diphosphine.

Graphical abstract: Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant
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