445417-39-0Relevant articles and documents
Cu(I)-catalyzed intramolecular cyclization of ene-carbamates: Synthesis of indoles and pyrrolo[2,3-c]pyridines
Barberis, Claude,Gordon, Thomas D.,Thomas, Christine,Zhang, Xiaolei,Cusack, Kevin P.
, p. 8877 - 8880 (2007/10/03)
Over the past few years, the use of palladium-catalyzed aromatic carbon-nitrogen bond forming reactions by the cross-coupling of aryl halides or triflates and amines has become a useful synthetic tool. Herein, we describe a copper(I) catalyst system that allows efficient synthesis of functionalized indoles and pyrrolo[2,3-c]pyridines. This method takes advantage of amino acid promoted copper coupling of amines with aryl halides, in particular, the use of the CuI/l-proline catalyst system.
Solid-phase synthesis of indolecarboxylates using palladium-catalyzed reactions
Yamazaki, Kazuo,Nakamura, Yosuke,Kondo, Yoshinori
, p. 6011 - 6019 (2007/10/03)
Polymer-supported, palladium-catalyzed cyclization reactions effectively synthesized indolecarboxylates. Palladium-catalyzed carbon - carbon bond-forming reactions of immobilized enaminoesters followed by transesterification yielded indole 2- or 3-carboxylates with various functional groups on the benzene ring. Indolecarboxylates were efficiently cyclized via an intramolecular palladium-catalyzed amination reaction of immobilized N-substituted dehydrohalophenylalanines, and immobilized N-acetyl-dehydroalanines were efficiently converted into indolecarboxylates via tandem Heck-amination reactions.
Palladium-catalyzed tandem C,N-arylation of immobilized enamine for solid phase indole synthesis
Yamazaki, Kazuo,Nakamura, Yosuke,Kondo, Yoshinori
, p. 2137 - 2138 (2007/10/03)
Intramolecular palladium-catalyzed N-arylation of immobilized dehydrohalophenylalaninate was found to proceed smoothly to form indolecarboxylates. The method was successfully combined with the Heck reaction to perform one pot indole synthesis via palladium-catalyzed tandem C,N-arylation reactions.
Design and synthesis of novel χ2-constrained phenylalanine, naphthylalanine, and tryptophan analogues and their use in biologically active melanotropin peptides
Wang, Wei,Cai, Minying,Xiong, Chiyi,Zhang, Junyi,Trivedi, Dev,Hruby, Victor J
, p. 7365 - 7374 (2007/10/03)
A series of novel hydrophobic, bulky χ2-constrained phenylalanine, naphthylalanine, and tryptophan derivatives was designed and synthesized. The key steps involved asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalyst
Design and synthesis of hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives
Wang, Wei,Zhang, Junyi,Xiong, Chiyi,Hruby, Victor J.
, p. 2137 - 2140 (2007/10/03)
A series of novel hydrophobic, bulky χ2-constrained phenylalanine and naphthylalanine derivatives were designed and synthesized. Asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh(I) catalysts generated high enantiomerically p
Practical, asymmetric synthesis of aromatic-substituted bulky and hydrophobic tryptophan and phenylalanine derivatives
Wang, Wei,Xiong, Chiyi,Zhang, Junyi,Hruby, Victor J
, p. 3101 - 3110 (2007/10/03)
Aromatic ring substituted tryptophans and phenylalanines can provide valuable tools in developing highly potent and selective peptide ligands with specific structural features in addition to providing a large lipophilic surface for binding to receptors and for crossing membrane barriers. An efficient method for the synthesis of these novel amino acids has been developed. In the approach, asymmetric hydrogenations of α-enamides using Burk's DuPHOS-based Rh (I) catalysts generated high enantiomerically pure α-amino acid derivatives, which subsequently underwent Suzuki cross couplings with boronic acid derivatives to afford these aromatic substituted amino acids in high yields and high enantioselectivity. The method can allow for the preparation of such amino acids in large scales for extensive structure-activity studies.
