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 (2006). Phase-Transfer-Catalyzed Enantioselective Mannich Reaction of Malonates with alfa-Amido Sulfones. ADVANCED SYNTHESIS & CATALYSIS, 348(15), 2043-2046 [10.1002/adsc.200600250].

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.
2006
F. Fini, L. Bernardi, R.P. Herrera, D. Pettersen, A. Ricci, V. Sgarzani (2006). Phase-Transfer-Catalyzed Enantioselective Mannich Reaction of Malonates with alfa-Amido Sulfones. ADVANCED SYNTHESIS & CATALYSIS, 348(15), 2043-2046 [10.1002/adsc.200600250].
F. Fini; L. Bernardi; R.P. Herrera; D. Pettersen; A. Ricci; V. Sgarzani
File in questo prodotto:
Eventuali allegati, non sono esposti

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/38107
 Attenzione

Attenzione! I dati visualizzati non sono stati sottoposti a validazione da parte dell'ateneo

Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 81
  • ???jsp.display-item.citation.isi??? 75
social impact