Pd(0)‐Catalyzed Heck‐Type Arylation of Didehydropeptides

Abstract Pd(0)‐catalyzed Heck‐type arylation of several didehydropeptides has been studied and the process has been found to be a viable method for the synthesis of the corresponding arylated products stereoselectively but in moderate yields.

[1]  J. Watanabe,et al.  Palladium(0)-catalyzed mizoroki-heck reaction and Rh(I)-catalyzed asymmetric hydrogenation of polymer-supported dehydroalanine system , 2003 .

[2]  C. Chai,et al.  N-Fmoc-dehydroalanine: a versatile molecular scaffold for the rapid solid-phase synthesis of cycloaliphatic amino acids , 2000 .

[3]  I. Beletskaya,et al.  The heck reaction as a sharpening stone of palladium catalysis. , 2000, Chemical reviews.

[4]  A. Ritzén,et al.  Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups , 1998 .

[5]  R. Middleton,et al.  Synthesis of 7-, 8- and 9-membered rings via endo Heck cyclisations of amino acid derived substrates , 1995 .

[6]  T. Singh,et al.  Design of peptides: Synthesis, crystal structure, molecular conformation, and conformational calculations of N‐Boc‐L‐Phe‐Dehydro‐Ala‐OCH3 , 1992, Biopolymers.

[7]  L. Hegedus,et al.  Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. 4 , 1989 .

[8]  T. Frejd,et al.  Palladium-Catalyzed Synthesis of Didehydroamino Acid Derivatives , 1989 .

[9]  U. Schmidt,et al.  Didehydroamino Acids (DDAA) and Didehydropeptides (DDP) , 1988 .

[10]  L. Hegedus,et al.  Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. 2. Total synthesis of the N-acetyl methyl ester of (.+-.)-clavicipitic acids , 1987 .

[11]  T. Jeffery.  HIGHLY STEREOSPECIFIC PALLADIUM-CATALYZED VINYLATION OF VINYLIC HALIDES UNDER SOLID-LIQUID PHASE TRANSFER CONDITIONS , 1985 .

[12]  T. Jeffery.  Highly stereospecific palladium-catalysed vinylation of vinylic halides under solid-liquid phase transfer conditions. , 1985 .

[13]  C. Shin,et al.  Dehydrooligopeptides. IV. Synthesis of Various Types of Dehydrodi-and tripeptides by Fragment Condensation and Base-Catalyzed β-Elimination , 1984 .

[14]  I. Ojima.  Homogeneous asymmetric catalysis by means of chiral rhodium complexes , 1984 .

[15]  F. Naso,et al.  Synthesis of dehydrophenylalanine derivatives by palladium catalyzed arylation of 2-acetamidoacrylic acid , 1983 .

[16]  Y. Shimohigashi,et al.  E/Z-Configurational assignment of dehydropeptides: Differential noe enhancement between the vinyl and amide protons of an α,β-dehydro amino acid derivative , 1982 .

[17]  J. Yoshimura,et al.  Dehydrooligopeptides. II. The Synthesis of Dehydrodehydrodipeptides by Direct Coupling and Base-catalyzed β-Elimination , 1981 .

[18]  E. P. Prokof'ev,et al.  The proton coupled 13C NMR direct determination of Z-, E-configuration of 4-benzyliden-2-phenyl(methyl)- Δ2-oxazolin-5-ones and products of their solvolysis , 1979 .