EnglishPd(II)-catalyzed cross-dehydrogenative coupling (CDC) of methyl N-phthaloyl dehydroalanine esters with simple aromatic hydrocarbons is reported. The reaction, which involves the cleavage of two sp(2) C–H bonds followed by C–C bond formation, stereoselectively generates highly valuable Z-dehydrophenylalanine skeletons in a practical, versatile, and atom economical manner. In addition, a perfluorinated product was expediently converted into important nonproteinogenic amino acid building blocks through copper-catalyzed conjugate additions of boron, silicon, and hydride moieties.
Palladium(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) of N-Phthaloyl Dehydroalanine Esters with Simple Arenes: Stereoselective Synthesis of Z-Dehydrophenylalanine Derivatives / Bartoccini, Francesca; Cannas, Diego Maria; FINI, Francesco; Piersanti, Giovanni. - In: ORGANIC LETTERS. - ISSN 1523-7060. - ELETTRONICO. - 18:11(2016), pp. 2762-2765.
| Data di pubblicazione: | 2016 |
| Titolo: | Palladium(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) of N-Phthaloyl Dehydroalanine Esters with Simple Arenes: Stereoselective Synthesis of Z-Dehydrophenylalanine Derivatives |
| Autore/i: | Bartoccini, Francesca; Cannas, Diego Maria; FINI, Francesco; Piersanti, Giovanni |
| Autore/i UNIMORE: | |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.1021/acs.orglett.6b01255 |
| Rivista: | |
| Volume: | 18 |
| Fascicolo: | 11 |
| Pagina iniziale: | 2762 |
| Pagina finale: | 2765 |
| Codice identificativo ISI: | WOS:000377319000062 |
| Codice identificativo Scopus: | 2-s2.0-84973495119 |
| Codice identificativo Pubmed: | 27206072 |
| Citazione: | Palladium(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) of N-Phthaloyl Dehydroalanine Esters with Simple Arenes: Stereoselective Synthesis of Z-Dehydrophenylalanine Derivatives / Bartoccini, Francesca; Cannas, Diego Maria; FINI, Francesco; Piersanti, Giovanni. - In: ORGANIC LETTERS. - ISSN 1523-7060. - ELETTRONICO. - 18:11(2016), pp. 2762-2765. |
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