Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Palladium Catalyzed Acetoxylation of Benzylic C-H Bonds Using a Bidentate Picolinamide Directing Group

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42196A, PaperTao Cheng, Weiyu Yin, Yi Zhang, Yingnan Zhang, Yong Huang
A general palladium catalyzed acetoxylation of benzylic C-H bonds has been developed. Picolinamides serve as an excellent directing group for the C-H activation of benzylic methyls. A wide scope of...
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Hypervalent iodine(III)-mediated cyclopropa(e)nation of alkenes/alkynes under mild conditions

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42123F, PaperShaoxia Lin, Mengru Li, Zhiyong Dong, Fushun Liang, Jingping Zhang
Hypervalent iodine(III)-mediated dioxygenation and diamination of alkenes have been previously developed. In this study, the potential application of hypervalent iodine(III) reagent was successfully extended to the dialkylation of unsaturated alkenes...
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Computational study of the glycylserine hydrolysis at physiological pH: zwitterionic versus anionic mechanism

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42372G, PaperTzvetan Traychev Mihaylov, Tatjana Parac-Vogt, Kristin Pierloot
The hydrolysis of GlySer at physiological pH was investigated by modeling the most feasible reaction mechanisms in aqueous phase at the MP2/6-311+(2df,2p)//SMD-M06/6-311+(2df,2p) level of the theory. To refine the energies...
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Investigation of Quantitative Structure-Reactivity Relationships in the Aliphatic Claisen Rearrangement of Bis-Vinyl Ethers Reveals a Dipolar, Dissociative Mechanism

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42011F, PaperNatasha F. O'Rourke, Jeremy E Wulff
Kinetic investigations of substituent effects in the thermal rearrangement of bis-vinyl ether substrates are reported. Findings indicate that the influence of the various substituent patterns on the rate of rearrangement...
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Gold nanoparticle (AuNPs) and Gold nanopore (AuNPore) catalysts in organic synthesis

14 January, 2014 - 12:54
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42207K, Review ArticleBalaram Takale, Ming Bao, Yoshinori Yamamoto
Organic synthesis using gold has gained tremendous attention is last few years, especially heterogeneous gold catalysis based on gold-nanoparticles has made its place in almost all organic reactions, because the...
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Convergent diversity-oriented side-chain macrocyclization scan for unprotected polypeptides

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,566-573
DOI: 10.1039/C3OB42168F, PaperYekui Zou, Alexander M. Spokoyny, Chi Zhang, Mark D. Simon, Hongtao Yu, Yu-Shan Lin, Bradley L. Pentelute
Here we describe a general synthetic platform for side-chain macrocyclization of an unprotected peptide library based on the SNAr reaction between cysteine thiolates and highly reactive perfluoroaromatic small molecule linkers.
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Nucleotide sensing with a perylene-based molecular receptor via amplified fluorescence quenching

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,561-565
DOI: 10.1039/C3OB41586D, CommunicationBappaditya Roy, Takao Noguchi, Daisuke Yoshihara, Youichi Tsuchiya, Arnab Dawn, Seiji Shinkai
The balanced molecular state of a guanidinium-tethered perylene-based fluorescence probe was conveniently used to achieve selective sensing of UTP, and the combination of equilibrium with molecular recognition further enhances the fluorescence sensitivity.
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Synthesis of substituted exo-glucals via a modified Julia olefination and identification as selective [small beta]-glucosidase inhibitors

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,690-699
DOI: 10.1039/C3OB41926F, PaperSamuel Habib, Florent Larnaud, Emmanuel Pfund, Teresa Mena Barragan, Thierry Lequeux, Carmen Ortiz Mellet, Peter G. Goekjian, David Gueyrard
A series of fluorine and non-fluorine-substituted C-glucosylidenes (exo-glucals) has been synthesized via a modified Julia olefination.
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Synthesis of thioamides via one-pot A3-coupling of alkynyl bromides, amines, and sodium sulfide

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,700-707
DOI: 10.1039/C3OB42275E, PaperYadong Sun, Huanfeng Jiang, Wanqing Wu, Wei Zeng, Jianxiao Li
We herein describe a novel method for the synthesis of thioamides by a three component condensation of alkynyl bromides, amines, and Na2S[middle dot]9H2O.
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Effect of configuration of 2-vinyldiazocarbonyl compounds on their reactivity: experimental and computational study

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,682-689
DOI: 10.1039/C3OB42102C, PaperMurat B. Supurgibekov, David Cantillo, C. Oliver Kappe, G. K. Surya Prakash, Valerij A. Nikolaev
The ability of non-fluorinated vinyldiazocarbonyl compounds to give pyrazoles is dictated by their configuration. The 3-CF3-substituted cis- or trans-analogues do not produce pyrazoles and on heating furnish only vinyloxocarbene derived products.
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The first synthesis of (-)-isoambreinolide, (+)-vitexifolin D and (+)-vitedoin B

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,667-672
DOI: 10.1039/C3OB42122H, PaperHanane Bouanou, Ruben Tapia, M. Jose Cano, Jose M. Ramos, Esteban Alvarez, Ettahir Boulifa, Abdelaziz Dahdouh, Ahmed I. Mansour, Ramon Alvarez-Manzaneda, Rachid Chahboun, Enrique Alvarez-Manzaneda
The treatment of [small delta],[varepsilon]-unsaturated carboxylic acids with iodine and triphenylphosphine leads to the corresponding spiro [gamma]-lactones in high yield and with complete stereoselectivity.
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Steric vs. electronic effects in the Lactobacillus brevis ADH-catalyzed bioreduction of ketones

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,673-681
DOI: 10.1039/C3OB42057D, PaperCristina Rodriguez, Wioleta Borzecka, Johann H. Sattler, Wolfgang Kroutil, Ivan Lavandera, Vicente Gotor
Steric or electronic effects: that is the question. A series of acetophenone derivatives differing in their size and electronic properties have been studied as substrates for Lactobacillus brevis ADH via hydrogen transfer. The results obtained have confirmed the versatility of this enzyme to accept bulky but electronically favored ketones.
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Bromo- and thiomaleimides as a new class of thiol-mediated fluorescence 'turn-on' reagents

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,557-560
DOI: 10.1039/C3OB42141D, CommunicationJudith Youziel, Ahmed R. Akhbar, Qadeer Aziz, Mark E. B. Smith, Stephen Caddick, Andrew Tinker, James R. Baker
Bromo- and thiomaleimides are shown to serve as highly effective quenchers of a covalently attached fluorophore. Reactions with thiols that lead to removal of the maleimide conjugation, or detachment of the fluorophore from the maleimide, result in 'turn-on' of the fluorescence.
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Total synthesis of (S)-14-azacamptothecin

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,637-642
DOI: 10.1039/C3OB41883A, PaperFeng Liu, Chaozhong Li
A new and concise synthesis of (S)-14-azacamptothecin has been accomplished in 8 steps from commercially available (R)-2-hydroxybutanoic acid.
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Electrophilic ipso-iodocyclization of N-benzyl-N-(1-naphthyl)propiolamides: synthesis of complex polycyclic lactams

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,643-650
DOI: 10.1039/C3OB42020E, PaperLi-Jing Wang, Hai-Tao Zhu, Yi-Feng Qiu, Xue-Yuan Liu, Yong-Min Liang
An intramolecular electrophilic ipso-iodocyclization of N-benzyl-N-(1-naphthyl)propiolamides combined with the Friedel-Crafts-type reaction for the synthesis of complex polycyclic lactams is reported.
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2-Arylacetic anhydrides as ammonium enolate precursors

14 January, 2014 - 12:54

Org. Biomol. Chem., 2014, 12,624-636
DOI: 10.1039/C3OB41869C, PaperLouis C. Morrill, Lyndsay A. Ledingham, Jean-Philippe Couturier, Jasmine Bickel, Andrew D. Harper, Charlene Fallan, Andrew D. Smith
2-Arylacetic anhydrides are convenient ammonium enolate precursors in isothiourea catalysed asymmetric intermolecular Michael addition-lactonisation processes.
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Organocatalytic Enantioselective Hydrophosphonylation of Aldehydes

12 January, 2014 - 12:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42403K, PaperRaquel P. Herrera, Juan V. Alegre-Requena, Eugenia Marques-Lopez, Pablo J. Sanz Miguel
We report our results concerning the first squaramide-catalysed hydrophosphonylation of aldehydes. In all cases, the reactions proceeded smoothly and cleanly under mild reaction conditions rendering final [small alpha]-hydroxy phosphonates in very...
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A recyclable and base-free method for the synthesis of 3-iodothiophenes by the iodoheterocyclisation of 1-mercapto-3-alkyn-2-ols in ionic liquids

12 January, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,651-659
DOI: 10.1039/C3OB41928B, PaperRaffaella Mancuso, Christian S. Pomelli, Cinzia Chiappe, Richard C. Larock, Bartolo Gabriele
The first example of an iodocyclization reaction carried out in a recyclable ionic liquid medium is reported.
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Asymmetric synthesis of drug-like spiro[chroman-3,3[prime or minute]-indolin]-2[prime or minute]-ones through aminal-catalysis

12 January, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,574-580
DOI: 10.1039/C3OB42100G, PaperDhevalapally B. Ramachary, M. Shiva Prasad, S. Vijaya Laxmi, R. Madhavachary
An interesting reflexive-Michael (r-M) reaction has been developed to access drug-like spiro[chroman-3,3[prime or minute]-indolin]-2[prime or minute]-ones in good yields with excellent ee's and de's using aminal-catalysis.
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The thermodynamics of the self-assembly of covalently linked oligomeric naphthalenediimides into helical organic nanotubes

12 January, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,607-614
DOI: 10.1039/C3OB41761A, PaperKoujiro Tambara, John-Carl Olsen, David E. Hansen, G. Dan Pantos
The mechanism and thermodynamic functions of the self-assembly of a family of covalently linked oligomeric naphthalenediimides (NDIs) were investigated through variable-temperature NMR and CD studies.
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