Organocatalytic asymmetric conjugate addition to allenic esters and ketones

…, GD Salla, J Overgaard, KA Jørgensen

Index: Poulsen, Thomas B.; Bernardi, Luca; Aleman, Jose; Overgaard, Jacob; Jorgensen, Karl Anker Journal of the American Chemical Society, 2007 , vol. 129, # 2 p. 441 - 449

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Citation Number: 69

Abstract

The first example of an organocatalytic enantioselective conjugate addition of cyclic β- ketoesters and glycine imine derivatives to electron-deficient allenes is described. We disclose that the corresponding chiral β, γ-unsaturated carbonyl compounds are formed exclusively under phase-transfer conditions using either cinchona-alkaloid-derived or biphenyl-based chiral quaternary ammonium salts as catalysts. The scope of the reaction ...