EnglishWe describe a biomimetic organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to imines. This simple protocol makes use of readily available Cinchona-derived organocatalysts and nucleophiles at the carboxylate oxidation state. The resulting beta-amino thioesters, being attractive precursors for the preparation of optically active beta-amino acids, are formed in good yields and in up to 79% ee. As suggested by several mechanistic insights the desired products are formed via initial formation of a thioester acetate enolate via decarboxylation of the malonic acid half thioester, followed by addition to the imine.
Organocatalytic Enantioselective Decarboxylative Addition of Malonic Half Thioesters to Imines / Ricci, Alfredo; Pettersen, Daniel; Bernardi, Luca; Fini, Francesco; Fochi, Mariafrancesca; Herrera, Raquel P.; Sgarzani, Valentina. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 349:7(2007), pp. 1037-1040.
| Data di pubblicazione: | 2007 |
| Titolo: | Organocatalytic Enantioselective Decarboxylative Addition of Malonic Half Thioesters to Imines |
| Autore/i: | Ricci, Alfredo; Pettersen, Daniel; Bernardi, Luca; Fini, Francesco; Fochi, Mariafrancesca; Herrera, Raquel P.; Sgarzani, Valentina |
| Autore/i UNIMORE: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1002/adsc.200600536 |
| Rivista: | |
| Volume: | 349 |
| Fascicolo: | 7 |
| Pagina iniziale: | 1037 |
| Pagina finale: | 1040 |
| Codice identificativo ISI: | WOS:000246990200007 |
| Codice identificativo Scopus: | 2-s2.0-34547186720 |
| Citazione: | Organocatalytic Enantioselective Decarboxylative Addition of Malonic Half Thioesters to Imines / Ricci, Alfredo; Pettersen, Daniel; Bernardi, Luca; Fini, Francesco; Fochi, Mariafrancesca; Herrera, Raquel P.; Sgarzani, Valentina. - In: ADVANCED SYNTHESIS & CATALYSIS. - ISSN 1615-4150. - STAMPA. - 349:7(2007), pp. 1037-1040. |
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