38256-56-3Relevant articles and documents
Synthesis of (+)-(R)-methyl 2-aminotetraline-2-carboxylate: The hydroxypinanone method versus the bislactim method
Solladie-Cavallo, Arlette,Martin-Cabrejas, Luisa M.,Caravatti, Giorgio,Lang, Marc
, p. 967 - 969 (2001)
The methyl ester of 2-aminotetraline-2-carboxylic acid (Atc-OMe), an important residue for modified peptides, could only be synthesized from the Schoellkopf bislactim method, the hydroxypinanone method leading, during the second step, to elimination inste
A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid
Elmehriki, Adam A. H.,Gleason, James L.
supporting information, p. 9729 - 9733 (2019/12/02)
Cyclic α-quaternary carbon stereocenters were prepared from biselectrophillic substrates and an easily prepared chiral bicyclic sulfonyl lactam. This was achieved in two steps by spiroalkylation, employing biphasic reaction conditions with a phase-transfer catalyst, followed by reduction and alkylation with a series of alkyl halide electrophiles. The products of this method were isolated in good yields with with high levels of diastereoselectivity. This methodology was employed in the enantioselective total synthesis of (R)-puraquinonic acid (1) for a late-stage installation of the α-quaternary carbon stereocenter. This enabled the shortest synthesis of 1 to date, an eight-pot sequence providing an overall yield of 14%.
Sulfones as Synthetic Linchpins: Transition-Metal-Free sp3–sp2 and sp2–sp2 Cross-Couplings Between Geminal Bis(sulfones) and Organolithium Compounds
Trost, Barry M.,Kalnmals, Christopher A.
supporting information, p. 9066 - 9074 (2018/06/29)
A valuable umpolung strategy that highlights the ambiphilic nature of the bis(phenylsulfonyl)methyl synthon and demonstrates its utility as a synthetic linchpin is reported. Although the bis(phenylsulfonyl)methyl group is typically introduced as an sp3-carbon nucleophile, it is demonstrated that it can also function as an effective sp2-carbon electrophile in the presence of organolithium nucleophiles. Alkyl- and aryllithiums couple with the central carbon of the bis(phenylsulfonyl)methyl unit to ultimately generate trisubstituted alkenes, comprising formal sp3–sp2 and sp2–sp2 cross-couplings between organolithium reagents and bis(sulfones). This process occurs almost instantaneously at ?78 °C in the absence of any transition metals. By developing this curious transformation, it has been demonstrated that bis(phenylsulfonyl)methane is a valuable synthetic linchpin, which can undergo two C?C bond-forming processes as an sp3-nucleophile, followed by a third C?C bond-forming reaction as an effective sp2-electrophile. This discovery significantly enhances the utility of this ubiquitous, but underutilized, linker group.
GROUP 8 TRANSITION METAL CATALYSTS AND METHOD FOR MAKING SAME AND PROCESS FOR USE OF SAME IN OLEFIN DISPROPORTIONATION REACTIONS
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Page/Page column 34; 35, (2017/12/09)
These catalyst compounds are represented by the formula (I and VI): wherein M is a Group 8 metal; X is an anionic ligand; L is a neutral two-electron donor ligand; A is a monotopic or ditopic chelating ligand. The present invention also relates to an easy applicable catalyst synthesis and the application in different olefin metathesis processes, e.g. Reaction Injection Molding (RIM), rotational molding, vacuum infusion, vacuum forming, process for conversion of fatty acids and fatty acid esters or mixtures thereof, in -olefins, dicarboxylic acids or dicarboxylic esters, etc.
A new synthesis of indoles via intramolecular cyclization of ?-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/03/05)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ?-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-
A new synthesis of indoles via intramolecular cyclization of ο-alkynyl N,N-dialkylanilines promoted by KOt-Bu/DMSO
Chen, Yan-Yan,Chen, Jia-Hua,Zhang, Niu-Niu,Ye, Lin-Miao,Zhang, Xue-Jing,Yan, Ming
supporting information, p. 478 - 481 (2015/04/27)
2-Aryl indoles could be prepared in excellent yields via the intramolecular cyclization of ο-alkynyl N,N-dialkylanilines. The reaction is efficiently promoted by the catalytic amount of KOt-Bu in DMSO at room temperature. A reaction mechanism involving α-
General procedure for the synthesis of ortho-vinylbenzyl-substituted amines, ethers, and sulfides
Shcheglova,Kolesnik,Ashirov
, p. 1329 - 1334 (2013/11/06)
A convenient procedure has been proposed for the synthesis ortho-vinylbenzyl-substituted ethers, amines, and sulfides via reaction of o-(2-bromoethyl)benzyl bromide with various nucleophiles.
A new phenylalanine derivative acts as an antagonist at the AMPA Receptor GluA2 and introduces partial domain closure: Synthesis, resolution, pharmacology, and crystal structure
Szymańska, Ewa,Frydenvang, Karla,Contreras-Sanz, Alberto,Pickering, Darryl S.,Frola, Elena,Serafimoska, Zorica,Nielsen, Birgitte,Kastrup, Jette S.,Johansen, Tommy N.
supporting information; experimental part, p. 7289 - 7298 (2011/12/04)
In order to map out molecular determinants for competitive blockade of AMPA receptor subtypes, a series of 2-carboxyethylphenylalanine derivatives has been synthesized and pharmacologically characterized in vitro. One compound in this series, (RS)-3h, showed micromolar affinity for GluA1o and GluA2(R)o receptors with an approximately 4-fold preference for GluA1/2 vs GluA3/4. In TEVC electrophysiological experiments (RS)-3h competitively antagonized GluA2(Q)i receptors. The X-ray structure of the active enantiomer (S)-3h in complex with GluA2-S1S2J showed a domain closure around 8°. Even though the nitro and the carboxyethyl groups of (S)-3h were both anchored to Tyr702 through a water H-bond network, these interactions only induced weak subtype selectivity. In spite of the fact that (S)-3h induced a domain closure close to that observed for partial agonists, it did not produce agonist responses at GluA2 receptors under nondesensitizing conditions. 2-Carboxyethylphenylalanine derivatives provide a new synthetic scaffold for the introduction of substituents that could lead to AMPA receptor subtype-selective ligands.
INHIBITORS OF BETA-SECRETASE
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Page/Page column 76, (2010/10/03)
The present invention is directed to a compound represented by the following structural formula or a pharmaceutically acceptable salt thereof. Pharmaceutical compositions and method of use of the compounds are also described.
7-Spirobenzocyclohexyl derivatives of naltrexone, oxymorphone, and hydromorphone as selective opioid receptor ligands
Fang, Xinqin,Larson, Dennis L.,Portoghese, Philip S.
, p. 3064 - 3070 (2007/10/03)
On the basis of previous structure-activity studies of the highly potent and selective δ-opioid receptor antagonist naltrindole (1) and the spiroindanyl analagues 2 and 3, we have synthesized epimeric pairs of spirobenzocyclohexyl derivatives of naltrexon