64889-55-0Relevant articles and documents
Taking control of P1, P1′ and double bond stereochemistry in the synthesis of Phe-Phe (E)-alkene amide isostere dipeptidomimetics
Wiktelius, Daniel,Luthman, Kristina
, p. 603 - 605 (2007)
A protocol for the stereocontrolled independent preparation of Phe-Phe trans-vinyl amide isostere dipeptideomimetics was developed based on a Wittig-type reaction. In the reaction two chiral building blocks were joined with excellent E-selectivity to give
Stereoselective Synthesis of 1,2-trans-Diamines Using the Three-Component Borono-Mannich Condensation – Reaction Scope and Mechanistic Insights
Norsikian, Stéphanie,Beretta, Margaux,Cannillo, Alexandre,Auvray, Marie,Martin, Amélie,Retailleau, Pascal,Iorga, Bogdan I.,Beau, Jean-Marie
, p. 1940 - 1951 (2017/04/21)
The Petasis borono-Mannich (PBM) process with easily accessible N-protected α-amino aldehydes produces 1,2-trans-diamines diastereoselectively with an enantiomeric excess up to 98 %. The protecting group on the nitrogen atom had a decisive influence on bo
Asymmetric hydroformylation of Z -Enamides and enol esters with rhodium-bisdiazaphos catalysts
Abrams, M. Leigh,Foarta, Floriana,Landis, Clark R.
supporting information, p. 14583 - 14588 (2015/01/08)
Asymmetric hydroformylation (AHF) of Z-enamides and Z-enol esters provides chiral, alpha-functionalized aldehydes with high selectivity and atom economy. Rh-bisdiazaphospholane catalysts enable hydroformylation of these challenging disubstituted substrates under mild reaction conditions and low catalyst loadings. The synthesis of a protected analog of l-DOPA demonstrates the utility of AHF for enantioselective, atom-efficient synthesis of peptide precursors.
Nucleophile-dependent regioselective reaction of (S)-4-benzyl-2- fluoroalkyl-1,3-oxazolines
Jiang, Haizhen,Yan, Liuming,Xu, Minjun,Lu, Wenjun,Cai, Yeshan,Wan, Wen,Yao, Jianhua,Wu, Shaoxiong,Zhu, Shizheng,Hao, Jian
, p. 4261 - 4269 (2013/06/26)
Nucleophile-dependent regioselectivities in the nucleophilic reaction of (S)-4-benzyl-2-fluoroalkyl-1,3-oxazoline to different types of fluorinated compounds were investigated experimentally and theoretically. The ring opening of (S)-4-benzyl-2-bromodifluoromethyl-1,3-oxazoline by arenethiolates exclusively occurred at the C5 position of the 1,3-oxazoline ring, whereas completely different regioselectivity was observed for a unimolecular radical nucleophilic substitution (SRN1) at the terminal bromine atom of the CF2Br group when arenolates were employed as the nucleophiles. The reaction of (S)-4-benzyl-2-trifluoromethyl-1,3-oxazoline with nucleophiles such as arenethiols, arenols, and TMSCl underwent nucleophilic ring opening in a regiospecific way, while the use of TMSCF3 was determined to proceed through nucleophilic addition to the C=N bond.
A facile one-pot synthesis of 2-fluoroalkyl 1,3-imidazolines and 1,3-oxazolines through imidoyl halide intermediates
Jiang, Haizhen,Sun, Lan,Yuan, Shijie,Lu, Wenjun,Wan, Wen,Zhu, Shizheng,Hao, Jian
supporting information; experimental part, p. 2858 - 2863 (2012/05/05)
A facile one-pot procedure has been developed for the synthesis of 1,3-imidazolines and 1,3-oxazolines bearing fluorinated alkyl groups at the 2-position. The reaction involves the condensation of N-monosubstituted ethane-1,2-diamines or 2-aminoethanols with a fluorinated carboxylic acid in the presence of PPh3/CX4. The proposed mechanism is that the amide intermediates were initially formed, and then converted to the imidoyl halide intermediates in the presence of PPh3/CX4, followed by rapid intramolecular cyclization to 1,3-diazoline products. This protocol allows for the synthesis of 2-bromodifluoromethyl-1,3-imidazoline, a useful CF2Br-heterocyclic building block, which can be used for the synthesis of gem-difluoromethylene linked compounds.
Synthesis of new fluorous modular chiral ligand derivatives from amino alcohols and application in enantioselective carbon-carbon bond-forming alkylation reactions
Sehnem, Jasquer A.,Milani, Priscila,Nascimento, Vanessa,Andrade, Leandro H.,Dorneles, Luciano,Braga, Antonio L.
experimental part, p. 997 - 1003 (2010/08/22)
N-Trifluoracyl β-chalcogeno amides and N-perfluoracyl β-thio amide ligands were prepared by a simple and efficient reaction sequence. These new ligands were evaluated in palladium-catalyzed alkylation of rac-(E)-1,3-diphenyl-2-propenyl acetate in the pres
Improved synthesis of phenylethylamine derivatives by Negishi cross-coupling reactions
Goddard, Craig M.L.,Massah, Ahmad Reza,Jackson, Richard F.W.
scheme or table, p. 9175 - 9181 (2011/01/12)
Trifluoroacetamido-protected β-aminoalkylzinc iodides undergo Negishi cross-coupling reaction with aryl iodides in moderate to excellent yields (42-84%) based on the corresponding trifluoroacetamido-protected β-aminoalkyl iodides, employing a catalyst pre
Discovery of a novel series of biphenyl benzoic acid derivatives as highly potent and selective human β3 adrenergic receptor agonists with good oral bioavailability. Part II
Imanishi, Masashi,Itou, Shinji,Washizuka, Kenichi,Hamashima, Hitoshi,Nakajima, Yutaka,Araki, Takanobu,Tomishima, Yasuyo,Sakurai, Minoru,Matsui, Shigeo,Imamura, Emiko,Ueshima, Koji,Yamamoto, Takao,Yamamoto, Nobuhiro,Ishikawa, Hirofumi,Nakano, Keiko,Unami, Naoko,Hamada, Kaori,Matsumura, Yasuhiro,Takamura, Fujiko,Hattori, Kouji
experimental part, p. 4002 - 4020 (2009/05/07)
The left-hand side (LHS) and central part of our first generation biphenyl (FGB) series was modified to improve in vitro and in vivo β3-AR potency without loss of oral bioavailability. First, in this study, we focused our efforts on replacement of the 3-chlorophenyl moiety in the LHS of FGB analogues with 3-pyridyl ring analogues to adjust the lipophilicity. Second, we investigated the replacement of the central part of this series and discovered that introduction of a methyl group into the α-position of the phenethylamine moiety greatly enhanced potency keeping good oral availability. Finally, the replacement of the two carbon linker of the central part with an ethoxy-based linker provided improved potency and PK profiles. As a result of these studies, several analogues (i.e., 9h, 9k, 91, 10g, 10m, 10p, 10r, 11b, and 11l) were identified that displayed an excellent balance of very higher human β3-AR potency compared to the FGB compounds, high selectivity, and good pharmacokinetic profiles. Furthermore, these several compounds showed high in vivo efficacy in an overactive bladder (OAB) model. These findings suggest that our selected second generation biphenyl (SGB) series compounds may be attractive new successful therapeutic candidates for the treatment of OAB.
