Org. and Biomol. Chem.

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From [small alpha]-nucleophiles to functionalized aggregates: exploring the reactivity of hydroxamate ion towards esterolytic reactions in micelles

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02067G, Review ArticleNamrata Singh, Yevgen Karpichev, Rahul Sharma, Bhanushree Gupta, Arvind K. Sahu, Manmohan L. Satnami, Kallol K. Ghosh
Hydroxamate ions as [small alpha]-nucleophiles for esterolytic reactions in water and micelles.
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Transition-Metal-Free C-H Oxidative Activation: Persulfate-Promoted Selective Benzylic Mono- and Difluorination

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02418D, CommunicationWen-Bin Yi, Chun Cai, Jing-jing Ma, Guo-ping Lu
An operationally simple and selective method for the direct conversion of benzylic C-H to C-F to get the mono- and difluoromethylated arenes using SelecfluorTM as a fluorine source was developed....
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Exploring the relationship between conformation and pKa: Can a pKa value be used to determine the conformational equilibrium?

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02630F, PaperJacob Ingemar Olsen, Stephan Sauer, Christian Marcus Pedersen, Mikael Bols
Four substituted cis and trans-4,5-dihydroxyhexahydropyridazines that were expected to undergo pH induced conformational switching were synthesized and carefully investigated by NMR analyzes and calculations. For two of the compounds a...
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Xanthenones: Calixarenes-catalyzed Syntheses, Anticancer Activity and QSAR Studies

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02611J, PaperDaniel L. da Silva, Bruna Silva Terra, Mateus Ribeiro Lage, Ana Lucia Ruiz, Cameron Capeletti da Silva, Joao Carvalho, J. Walkimar de M. Carneiro, Felipe Terra Martins, Sergio Antonio Fernandes, Angelo de Fatima
An efficient method is proposed for obtaining tetrahydrobenzo[a]xanthene-11-ones and tetrahydro-[1,3]-dioxolo[4,5-b]xanthen-9-ones. The method is based on the use of p-sulfonic acid calix[n]arenes as catalysts under solvent-free condition.The antiproliferative activity of fitity-nine...
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Enantio-pure synthesis of dihydrobenzo[1,4]-oxazine-3-carboxylic acids and approach to benzoxazinyl oxazolidinones

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02475C, PaperRajesh Malhotra, Tushar K Dey, Sourav Basu, Saumen Hajra
A two steps protocol is developed for the efficient synthesis of enantiopure N-Boc-dihydrobenzo[b]-1,4-oxazine-3-carboxylic acids 4 from serine derived cyclic sulfamidate via intramolecular arylamination. RuPhospalladacycle alongwith additional RuPhos ligand is found...
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In situ activation of benzyl alcohols with XtalFluor-E: formation of 1,1-diarylmethanes and 1,1,1-triarylmethanes through Friedel-Crafts benzylation

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02655A, CommunicationJustine Desroches, Pier Alexandre Champagne, Yasmine Benhassine, Jean-Francois Paquin
The Friedel-Crafts benzylation of arenes using benzyl alcohols activated in situ with XtalFluor-E is described. A wide range of 1,1-diarylmethanes and 1,1,1-triarylmethanes were prepared under simple and mild conditions, without the need for a transition metal or a strong Lewis acid.
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A new multicomponent reaction: Unexpected formation of derivatizable cyclic [small alpha]-alkoxy isothioureas

25 January, 2015 - 07:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02608J, PaperFabian Brockmeyer, Valentin Morosow, Jurgen Martens
An unexpected formation of cyclic [small alpha]-alkoxy isothioureas has been achieved. As is known, the heterocyclic imines 2,5-dihydro-1,3-thiazoles are convertible to bisamides with the aid of a carboxylic acid and an...
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Synthesis of a [small beta]-CCT-lanthanide conjugate for binding the dopamine transporter

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02165G, CommunicationGregory R. Naumiec, Grace Lincourt, Jeremy P. Clever, Michael A. McGregor, Abraham Kovoor, Brenton DeBoef
The development of a [small beta]-CCT-lanthanide conjugate that binds the dopamine transporter (DAT) with high affinity (Kd = 303 nM) is described. This molecular probe could be used for in vivo or in vitro studies of the DAT via MRI, PET or SPECT.
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The enantioselective construction of tetracyclic diterpene skeletons with Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation reactions

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02489C, PaperSarah J. Burke, William P. Malachowski, Sharan K. Mehta, Roselyn Appenteng
Enantioselective synthesis of natural product-like structures from a two-step extension of the Birch-Cope sequence: intramolecular Friedel-Crafts alkylation and palladium-catalyzed cycloalkenylation.
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"One-pot" synthesis of amidoxime via Pd-catalyzed cyanation and amidoximation

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02456G, CommunicationChu-Ting Yang, Jun Han, Jun Liu, Mei Gu, Yi Li, Jun Wen, Hai-Zhu Yu, Sheng Hu, Xiaolin Wang
"One-pot" synthesis of amidoxime was developed for studies on the interactions between amidoxime and uranyl.
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Highly enantioselective catalytic 1,3-dipolar cycloadditions of [small alpha]-alkyl diazoacetates: efficient synthesis of functionalized 2-pyrazolines

25 January, 2015 - 07:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02372B, PaperSung Il Lee, Ka Eun Kim, Geum-Sook Hwang, Do Hyun Ryu
Chiral oxazaborolidinium ion catalyzed 1,3-dipolar cycloaddition reaction of [small alpha]-substituted diazoacetates gives functionalized 2-pyrazolines in high to excellent enantiomeric ratios.
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Halogenated boron-dipyrromethenes: synthesis, properties and applications

23 January, 2015 - 07:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02293A, Review ArticleVellanki Lakshmi, Malakalapalli Rajeswara Rao, Mangalampalli Ravikanth
Synthesis and properties of halogenated boron-dipyrromethenes and their applications in developing various BODIPY systems are described in this review.
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Bioreducible polyethylenimine nanoparticles for efficient delivery of nucleic acids

23 January, 2015 - 07:17
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02614D, PaperRuby Bansal, Shweta Tayal, K. C. Gupta, Pradeep Kumar
Recently, non-viral vectors for the nucleic acids delivery have received considerable attention. Among the various non-viral vectors, branched polyethylenimine (bPEI, 25 kDa) has been one of the most widely used...
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Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile

23 January, 2015 - 07:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02602K, CommunicationAlafate Adili, Zhong-Lin Tao, Dian-Feng Chen, Zhi-Yong Han
2-Amino-3-cyano-4H-chromenes show great potential as novel anticancer agents. Here we report a quinine-catalyzed highly enantioselective formal 4 + 2 cycloaddition of ortho-quinone methides and malononitrile, providing a unique approach to 4-arylvinyl, 4-aryl and 4-vinyl 2-amino-3-cyano-4H-chromenes with excellent yields and enantioselectivities.
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Primary amine recognition in water by a calix[6]aza-cryptand incorporated in dodecylphosphocholine micelles

23 January, 2015 - 07:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02495H, PaperEmilio Brunetti, Alex Inthasot, Flore Keymeulen, Olivia Reinaud, Ivan Jabin, Kristin Bartik
A zinc calix[6]azacryptand complex was incorporated into dodecylphosphocholine micelles. This complex can strongly and selectively bind linear primary amines in an aqueous medium.
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Synthesis of locked cyclohexene and cyclohexane nucleic acids (LCeNA and LCNA) with modified adenosine units

23 January, 2015 - 07:17

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02193B, PaperMichal Sala, Milan Dejmek, Eliska Prochazkova, Hubert Hrebabecky, Jiri Rybacek, Martin Dracinsky, Pavel Novak, Sarka Rosenbergova, Jiri Fukal, Vladimir Sychrovsky, Ivan Rosenberg, Radim Nencka
We designed novel conformationally locked cyclohexene nucleic acid and studied their properties.
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Functional chromatographic technique for natural product isolation

21 January, 2015 - 06:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02292K, CommunicationEric C. Lau, Damian J. Mason, Nicole Eichhorst, Pearce Engelder, Celestina Mesa, E. M. Kithsiri Wijeratne, G. M. Kamal B. Gunaherath, A. A. Leslie Gunatilaka, James J. La Clair, Eli Chapman
Natural product discovery arises through a unique interplay between chromatographic purification and protein affinity.
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In tandem or alone: a remarkably selective transfer hydrogenation of alkenes catalyzed by ruthenium olefin metathesis catalysts

21 January, 2015 - 06:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02480J, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Grzegorz Krzysztof Zielinski, Cezary Samojlowicz, Tomasz Wdowik, Karol Grela
A remarkably selective system for transfer hydrogenation of alkenes, composed of Grubbs' ruthenium metathesis catalyst and HCOONa/HCOOH, is presented. This system can also be formed directly after a metathesis reaction to effect hydrogenation in a single-pot.
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Volatiles from nineteen recently genome sequenced actinomycetes

21 January, 2015 - 06:54

Org. Biomol. Chem., 2015, Advance Article
DOI: 10.1039/C4OB02609H, PaperChristian A. Citron, Lena Barra, Joachim Wink, Jeroen S. Dickschat
The volatiles from nineteen genome sequenced actinobacteria were analysed by GC/MS and the identified terpenes were correlated to genome data.
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Acid-promoted direct electrophilic trifluoromethylthiolation of phenols

21 January, 2015 - 06:54
Org. Biomol. Chem., 2015, Accepted Manuscript
DOI: 10.1039/C4OB02633K, PaperMarjan Jereb, Kaja Gosak
The electrophilic aromatic ring trifluoromethylthiolation of variously substituted phenols was accomplished by PhNHSCF3 (N-trifluoromethylsulfanyl)aniline 1 in the presence of BF3[middle dot]Et2O 2 or triflic acid as promoters. The functionalization was exclusively...
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