The highly enantioselective reaction between in situ generated, Cbz-protected azomethines and malonates in the presence of 150 mol% of potassium carbonate (50% w/w) and 1 mol% of quinine-derived quaternary ammonium bromides as phase-transfer organocatalysts has been developed. This study reports a novel approach for the asymmetric Mannich-type reaction and a wide range of azomethines, including those derived from enolizable aldehydes, is tolerated by the present system. The adducts, obtained in excellent yields with ee up to 98%, are suitable precursors of optically pure beta-amino acids.

Phase-Transfer-Catalyzed Enantioselective Mannich Reaction of Malonates with alpha-Amido Sulfones / Fini, Francesco; Bernardi, Luca; Herrera, Raquel P.; Pettersen, Daniel; Ricci, Alfredo; Sgarzani, Valentina. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 348:15(2006), pp. 2043-2046.

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