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 β-amino acids.

Phase-Transfer-Catalyzed Enantioselective Mannich Reaction of Malonates with alfa-Amido Sulfones

FINI, FRANCESCO;BERNARDI, LUCA;RICCI, ALFREDO MARCO;
2006

Abstract

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 β-amino acids.
F. Fini; L. Bernardi; R.P. Herrera; D. Pettersen; A. Ricci; V. Sgarzani
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/38107
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