Enantioselective Synthesis of Hydroxy-Substituted DBN-Type Amidines as Potential Chiral Catalysts

Autor: Ostendorf, Martin, Neut, Sandor van der, Rutjes, Floris P. J. T.
Zdroj: European Journal of Organic Chemistry; January 2000, Vol. 2000 Issue: 1 p105-113, 9p
Abstrakt: The synthesis and X-ray crystal structures of three enantiopure hydroxy-substituted amidines of the DBN-type are described. The key starting material, a 5-(phenylsulfonyl)pyrrolidin-2-one, was obtained by an oxazaborolidine-catalysed reductive desymmetrization of a meso-imide and was functionalized through N-acyliminium ion chemistry. The hydroxy groups were introduced by ozonolysis or reduction. Preliminary results on the use of the hydroxyamidines as chiral, bifunctional catalysts in selected Michael reactions are described.
Databáze: Supplemental Index