We 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. |
Tipologia | Articolo su rivista |
File in questo prodotto:
File | Descrizione | Tipologia | |
---|---|---|---|
10 - Adv. Synth. and Catal. 2007 Ricci 1037-1040.pdf | Articolo Principale | Versione dell'editore (versione pubblicata) | Administrator Richiedi una copia |

I documenti presenti in Iris Unimore sono rilasciati con licenza Creative Commons Attribuzione - Non commerciale - Non opere derivate 3.0 Italia, salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris