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EnglishThe 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.
| Titolo: | Phase-Transfer-Catalyzed Enantioselective Mannich Reaction of Malonates with alfa-Amido Sulfones |
| Autore/i: | FINI, FRANCESCO; BERNARDI, LUCA; R. P. Herrera; D. Pettersen; RICCI, ALFREDO MARCO; V. Sgarzani |
| Autore/i Unibo: | |
| Anno: | 2006 |
| Rivista: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/adsc.200600250 |
| 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. |
| Data prodotto definitivo in UGOV: | 2007-02-16 |
| Appare nelle tipologie: | 1.01 Articolo in rivista |
File in questo prodotto:
http://hdl.handle.net/11585/38107
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