Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Enantioselective synthesis of [small alpha],[small alpha]-difluoro-[small beta]-lactams using amino alcohol ligands

8 August, 2014 - 15:17

Org. Biomol. Chem., 2014, 12,6484-6489
DOI: 10.1039/C4OB01184H, PaperAtsushi Tarui, Takeshi Ikebata, Kazuyuki Sato, Masaaki Omote, Akira Ando
A practical and highly enantioselective Reformatsky reaction of ethyl bromodifluoroacetate with imines using a cheap and commercially available amino alcohol ligand is described.
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Enantioselective synthesis of [gamma]-tetrasubstituted nitrosulfonyl carboxylates and amides viaL-tert-leucine-derived-squaramide catalyzed conjugate addition of nitrosulfones to acrylates and acrylamides

8 August, 2014 - 15:17

Org. Biomol. Chem., 2014, 12,6425-6431
DOI: 10.1039/C4OB00344F, PaperKalisankar Bera, Irishi N. N. Namboothiri
A t-leucine-derived squaramide catalyzed reaction of [small alpha]-nitrosulfones with acrylates/acrylamides provides [gamma]-tetrasubstituted [gamma]-nitro-[gamma]-sulfonyl carboxylates/amides in excellent yield and enantioselectivity.
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Electrochemical and theoretical analysis of the reactivity of shikonin derivatives: dissociative electron transfer in esterified compounds

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6393-6398
DOI: 10.1039/C4OB01207K, PaperGeorgina Armendariz-Vidales, Carlos Frontana
Electrochemical and theoretical analysis of Shikonin derivatives revealed that for esterified compounds, a dissociative electron transfer process occurs.
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An unusual mulinane diterpenoid from the Chilean plant Azorella trifurcata (Gaertn) Pers

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6406-6413
DOI: 10.1039/C4OB00966E, PaperCarlos Areche, Beatriz Sepulveda, Aurelio San Martin, Olimpo Garcia-Beltran, Mario Simirgiotis, Alvaro Canete
An unusual mulinane diterpenoid named 7[small alpha]-acetoxy-9-epi-13[small beta]-hydroxymulinane was isolated from A. trifurcate. This compound possesses a new trans-syn-trans arrangement in a tricyclic ring system not previously encountered in nature.
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Efficient asymmetric synthesis of N-protected-[small beta]-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6507-6515
DOI: 10.1039/C4OB01047G, PaperRajesh Malhotra, Tushar K. Dey, Swarup Dutta, Sourav Basu, Saumen Hajra
First regioselective ring opening of serine derived cyclic sulfamidate with ArONa is developed to provide an easy and direct access of a variety of N-Boc- and N-PMB protected [small beta]-aryloxy-[small alpha]-amino acids with complete retention of enantiopurity in moderate to high yields.
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Amino acid chirons: a tool for asymmetric synthesis of heterocycles

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6297-6339
DOI: 10.1039/C4OB00943F, Review ArticlePriyanka Singh, Krishnananda Samanta, Sanjit Kumar Das, Gautam Panda
This review describes diverse asymmetric heterocycles with various membered rings (n = 3-9) for the period from 1996 to Dec. 2013.
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Aliphatic amine responsive organogel system based on a simple naphthalimide derivative

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6399-6405
DOI: 10.1039/C4OB00728J, PaperXinhua Cao, Tingting Zhang, Aiping Gao, Keli Li, Qiuli Cheng, Lijuan Song, Min Zhang
Aliphatic amines and aromatic amines were distinguished and detected by an organogel system containing naphthalimide.
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A hydrophobic disordered peptide spontaneously anchors a covalently bound RNA hairpin to giant lipidic vesicles

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6363-6373
DOI: 10.1039/C4OB00721B, PaperAlexandra Le Chevalier Isaad, Paolo Carrara, Pasquale Stano, Kollappillil S. Krishnakumar, Dominique Lafont, Alexandra Zamboulis, Rene Buchet, Denis Bouchu, Florian Albrieux, Peter Strazewski
Exergonic compartmentation of nucleic acids to liposomes through conjugation with peptides lends experimental support to early evolvable RNA-peptide 'collaboration'.
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Asymmetric synthesis of substituted NH-piperidines from chiral amines

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6384-6388
DOI: 10.1039/C4OB00657G, PaperLekh Nath Gautam, Yijin Su, Novruz G. Akhmedov, Jeffrey L. Petersen, Xiaodong Shi
Previously, we reported an efficient asymmetric synthesis of substituted piperidines through an exocyclic chirality induced nitroalkene/amine/enone (NAE) condensation reaction.
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DFT study on the reaction mechanisms and stereoselectivities of NHC-catalyzed [2 + 2] cycloaddition between arylalkylketenes and electron-deficient benzaldehydes

6 August, 2014 - 14:54

Org. Biomol. Chem., 2014, 12,6374-6383
DOI: 10.1039/C4OB00606B, PaperMengmeng Zhang, Donghui Wei, Yang Wang, Suiji Li, Jiefei Liu, Yanyan Zhu, Mingsheng Tang
Two possible mechanisms of ketene and aldehyde [2 + 2] cycloaddition catalyzed by NHC have been investigated using the DFT method.
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Relative contractile motion of the rings in a switchable palindromic [3]rotaxane in aqueous solution driven by radical-pairing interactions

4 August, 2014 - 14:17

Org. Biomol. Chem., 2014, 12,6089-6093
DOI: 10.1039/C4OB01228C, CommunicationLeah S. Witus, Karel J. Hartlieb, Yuping Wang, Aleksandrs Prokofjevs, Marco Frasconi, Jonathan C. Barnes, Edward J. Dale, Albert C. Fahrenbach, J. Fraser Stoddart
This communication describes a mechanically interlocked molecule (MIM), capable of switchable and reversible linear molecular motion.
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1,1,1,3,3,3-Hexafluoro-2-propanol and 2,2,2-trifluoroethanol solvents induce self-assembly with different surface morphology in an aromatic dipeptide

2 August, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,6181-6189
DOI: 10.1039/C4OB00821A, PaperSamala Murali Mohan Reddy, Ganesh Shanmugam, Asit Baran Mandal
1,1,1,3,3,3-Hexafluoro-2-propanol and 2,2,2-trifluoroethanol solvents, which are known to disaggregate self-assembled peptides, induce the self-assembly of aromatic dipeptides to give structures with different surface morphologies.
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Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

2 August, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,6121-6127
DOI: 10.1039/C4OB01142B, PaperAdam D. J. Calow, Elena Fernandez, Andrew Whiting
Efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from [small alpha],[small beta]-unsaturated aldehydes are reported.
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A fluorescent probe for intracellular cysteine overcoming the interference by glutathione

2 August, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,6128-6133
DOI: 10.1039/C4OB00382A, PaperMinggang Tian, Fuqiang Guo, Yuming Sun, Weijia Zhang, Fang Miao, Yong Liu, Guofen Song, Cheuk-Lam Ho, Xiaoqiang Yu, Jing Zhi Sun, Wai-Yeung Wong
A fluorescent probe was reported to discriminate 30-200 [small mu ]M cysteine, overcoming the interference by 1-10 mM glutathione. The selectivity was also proved by cellular experiments.
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Copper-catalyzed annulation of heteroaromatic [small beta]-halo-[small alpha],[small beta]-unsaturated carboxylic acids with alkynes for the synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6114-6120
DOI: 10.1039/C4OB00996G, PaperDa-Wei Gu, Xun-Xiang Guo
Efficient synthesis of indolo[2,3-c]pyrane-1-ones and thieno[2,3-c]pyrane-7-ones was achieved via annulation of heteroaromatic [small beta]-halo-[small alpha],[small beta]-unsaturated carboxylic acids with alkynes.
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TFAA/H3PO4 mediated unprecedented N-acylation of carbazoles leading to small molecules possessing anti-proliferative activities against cancer cells

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6080-6084
DOI: 10.1039/C4OB00686K, CommunicationSunder Kumar Kolli, Bagineni Prasad, P. Vijaya Babu, Mohd Ashraf Ashfaq, Nasreen Z. Ehtesham, R. Ramesh Raju, Manojit Pal
TFAA/H3PO4-mediated unusual N-acylation of carbazoles afforded potential anti-proliferative agents.
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Syntheses of thiol and selenol esters by oxidative coupling reaction of aldehydes with RYYR (Y = S, Se) under metal-free conditions

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6072-6075
DOI: 10.1039/C4OB01159G, CommunicationChunhuan He, Xuewei Qian, Peipei Sun
Thiol (selenol) esters were synthesized by a direct oxidative coupling reaction of aldehydes with disulfides (diselenides) under metal-free conditions.
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3-NO2-5,10,15-triarylcorrolato-Cu as a versatile platform for synthesis of novel 3-functionalized corrole derivatives

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6200-6207
DOI: 10.1039/C4OB01247J, PaperM. Stefanelli, M. Mancini, M. Raggio, S. Nardis, F. R. Fronczek, G. T. McCandless, K. M. Smith, R. Paolesse
By way of a [small beta]-acylated copper corrolate, a novel corrole derivative bearing an alkyl azide group on the peripheral positions was obtained and successfully exploited in click chemistry reactions.
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Deciphering aromaticity in porphyrinoids via adaptive natural density partitioning

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6145-6150
DOI: 10.1039/C4OB01018C, PaperAlexander S. Ivanov, Alexander I. Boldyrev
Aromaticity in porphyrins is described by the adaptive natural density partitioning analysis.
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The Escherichia coli glucuronylsynthase promoted synthesis of steroid glucuronides: improved practicality and broader scope

31 July, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,6208-6214
DOI: 10.1039/C4OB00984C, PaperPaul Ma, Nicholas Kanizaj, Shu-Ann Chan, David L. Ollis, Malcolm D. McLeod
Steroid glucuronides can be quickly and conveniently prepared on the milligram scale using the E. coli glucuronylsynthase enzyme followed by purification with solid-phase extraction.
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