Pd(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. [10.1021/acs.orglett.6b01255]

Palladium(II)-Catalyzed Cross-Dehydrogenative Coupling (CDC) of N-Phthaloyl Dehydroalanine Esters with Simple Arenes: Stereoselective Synthesis of Z-Dehydrophenylalanine Derivatives

FINI, Francesco;
2016

Abstract

Pd(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.
2016
20-mag-2016
18
11
2762
2765
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. [10.1021/acs.orglett.6b01255]
Bartoccini, Francesca; Cannas, Diego Maria; Fini, Francesco; Piersanti, Giovanni
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11380/1122083
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