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

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• 作者：Francesca Bartoccini ; Diego Maria Cannas ; Francesco Fini ; Giovanni Piersanti
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：June 3, 2016
• 年：2016
• 卷：18
• 期：11
• 页码：2762-2765
• 全文大小：339K
• 年卷期：0
• ISSN：1523-7052

文摘

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 sp² 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.