116838-52-9Relevant articles and documents
2-(1H-pyrrolyl)carboxylic acids as pigment precursors in garlic greening
Wang, Dan,Nanding, Husile,Han, Na,Chen, Fang,Zhao, Guanghua
, p. 1495 - 1500 (2008)
Six model compounds having a 2-(1H-pyrrolyl)carboxylic acid moiety and a hydrophobic R group were synthesized to study their effects on garlic greening, the structures of which are similar to that of 2-(3,4-dimethyl-1H-pyrrolyl)-3- methylbutanoic acid (PP
The synthesis of chiral 1-(1H-pyrrole) derivatives
Jefford, Charles W.,De Villedon De Naide, Fabienne,Sienkiewicz, Krzysztof
, p. 1069 - 1076 (1996)
Enantiomerically pure primary amines possessing an epimerizable center, such as α-amino acids and their ester hydrochlorides, undergo condensation with tetrahydro-2,5-dimethoxyfuran 2 in acetic acid or acetic acid containing sodium acetate at 80°C for 30
Short, enantiogenic syntheses of (-)-indolizidine 167b and (+)-monomorine
Jefford, Charles W.,Tang, Qian,Zaslona, Alexander
, p. 3513 - 3518 (1991)
The enantiogenic syntheses of (-)-indolizidinc 167B (1) and (+)-monomorine (2) are described. D-Norvaline and L-alanine are converted into their 1-pyrrole derivatives by reaction with 2,5-dimethoxytetrahydrofuran. Thereafter, Arndt-Eistert homologation of the N-alkanoic acid substituent, followed by rhodium(II) acetate catalyzed decomposition of its α-diazo ketone derivative, provides the relevant bicyclic precursors, the vested chirality of which directs catalytic hydrogenation affording 1 and 2. Provision for the 5-butyl side chain in 2 is made by prior Lewis acid catalyzed rearrangement of the mixed anhydride obtained from butyryl chloride and the pyrrole analogue of L-alanine.
Friedel-Crafts alkylation of natural amino acid-derived pyrroles with CF3-substituted cyclic imines
Shmatova, Olga I.,Shevchenko, Nikolay E.,Balenkova, Elizabeth S.,R?schenthaler, Gerd-Volker,Nenajdenko, Valentine G.
, p. 92 - 93 (2013)
Natural amino acid-derived ethyl 2-(1-pyrrolyl)alkanoates react with 2-trifluoromethyl-1-azacycloalkenes selectivity at the β-position of the pyrrole moiety to afford ethyl 2-[3-(1-trifluoromethyl-2-azacycloalkyl)pyrrol-1- yl]alkanoates.
Catalytic Hydrogenation of N-protected α-Amino Acids Using Ruthenium Complexes with Monodentate Phosphine Ligands
Saito, Akari,Yoshioka, Shota,Naruto, Masayuki,Saito, Susumu
, p. 424 - 429 (2019/11/28)
A ruthenium complex with a monodentate phosphine ligand was used to catalytically hydrogenate N-protected α-amino acids under essential retention of the configuration of their α-chiral centers. Among the ligands tested for this hydrogenation, which proceeds at a relatively low temperature, tris(para-fluorophenyl)phosphine exhibited the best performance. In comparison, electron-rich monodentate, bidentate, and tridentate phosphines were far less effective. The precatalyst Ru(OAc)2[(p-FC6H4)3P]2 was synthesized and isolated, and its structure was determined by a single-crystal X-ray diffraction analysis. N-protected α-amino acids with neutral alkyl side chains, including polar functional groups such as sulfides, indoles, ethers, phenols, pyrroles, and arenes, are compatible with the applied hydrogenation conditions, affording the corresponding optically active 2-substituted-2-(1H-pyrrol-1-yl)ethan-1-ol (2-amino ethanol) derivatives in moderate to high yield. (Figure presented.).
Enantioselective Synthesis of N-Benzylic Heterocycles: A Nickel and Photoredox Dual Catalysis Approach
Pezzetta, Cristofer,Bonifazi, Davide,Davidson, Robert W. M.
supporting information, p. 8957 - 8961 (2019/11/11)
Reported herein is a dual nickel- and photoredox-catalyzed modular approach for the preparation of enantioenriched N-benzylic heterocycles. α-Heterocyclic carboxylic acids, easily obtainable from common commercial material, are reported as suitable substrates for a decarboxylative strategy in conjunction with a chiral pyridine-oxazoline (PyOx) ligand, providing quick access to enantioenriched drug-like products. The presence of a directing group on the heterocyclic moiety is shown to be beneficial, affording improved stereoselectivity in a number of cases.
Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores
Kumar, N.N. Bhuvan,Mukhina, Olga A.,Kutateladze, Andrei G.
supporting information, p. 9608 - 9611 (2013/07/26)
Enantiopure alkaloid mimics are synthesized via high yielding intramolecular cycloadditions of photogenerated azaxylylenes tethered to pyrroles, with further growth of molecular complexity via post-photochemical transformations of primary photoproducts. This expeditious access to structurally unprecedented polyheterocyclic cores is being developed in the context of diversity-oriented synthesis, as the modular design allows for rapid "pre-assembly" of diverse photoprecursors from simple building blocks/diversity inputs.
Synthesis and characterization of chiral conducting polymers based on polypyrrole
Chen, Fang,Akhtar, Parveen,Kane-Maguire, Leon A. P.,Wallace, Gordon G.
, p. 939 - 945 (2007/10/03)
A range of optically active pyrrole monomers have been synthesized in which achiral substituent is covalently bonded either to the pyrrole N or C3 ring position, namely (-)(1R)-4-methyl-N-(1-phenylethyl)pyrrole-3-carboxamide, (+)-(1S)-4-methyl-N-(1-phenyl
Peptide Synthesis Using the Pyrrole Ring as an Amino Protecting Group
Kashima, Choji,Maruyama, Tatsuya,Harada, Kazuo,Hibi, Shigeki,Omote, Yoshimori
, p. 601 - 645 (2007/10/02)
The utility of a pyrrole ring as an amino protecting group for amino acids in peptide synthesis has been studied.The N-termini of various amino acids (1) were protected with a pyrrole ring by treatment with 2,5-dimethoxytetrahydrofuran (10) to give 2-substituted 2-(1-pyrrolyl)acetic acids (11).The peptide bond between (11) and amino acid methyl ester (2) was formed using N,N'-dicyclohexylcarbodiimide, and the pyrrole ring was cleaved by ozonolysis and hydrolysis without the cleavage of a peptide bond to give the corresponding dipeptide compounds (26) in good yields.
