Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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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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Enantioselective bacterial hydrolysis of amido esters and diamides derived from (+/-)-trans-cyclopropane-1,2-dicarboxylic acid

12 January, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,615-623
DOI: 10.1039/C3OB42066C, PaperKatharina G. Hugentobler, Francisca Rebolledo
Amidase from Rhodococcus rhodochrous enantioselectively catalyzes the hydrolysis of different racemic diamides (rac-10) and amido esters derived from trans-cyclopropane-1,2-dicarboxylic acid.
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Rh-catalyzed allylic C-F bond activation: the stereoselective synthesis of trisubstituted monofluoroalkenes and a mechanism study

12 January, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,581-588
DOI: 10.1039/C3OB42038H, PaperHe Zhang, Jin-Hong Lin, Ji-Chang Xiao, Yu-Cheng Gu
Rhodium-catalyzed allylic C-F bond activation was found to be a promising approach for the conversion of allylic difluoro-homoallylic alcohols into trisubstituted monofluoroalkenes in good yields with excellent stereoselectivity.
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Design of an environmentally sensitive fluorescent 8-aza-7-deaza-2[prime or minute]-deoxyadenosine derivative with dual fluorescence for the specific detection of thymine

10 January, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,660-666
DOI: 10.1039/C3OB41757C, PaperAzusa Suzuki, Nobukatsu Nemoto, Isao Saito, Yoshio Saito
A novel environmentally sensitive fluorescent (ESF) purine nucleoside, cnaA, was synthesized and its photophysical properties were investigated.
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Photoresponsive vesicle permeability based on intramolecular host-guest inclusion

10 January, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,600-606
DOI: 10.1039/C3OB41893F, PaperUlrike Kauscher, Avik Samanta, Bart Jan Ravoo
Azobenzene-appended amphiphilic cyclodextrins enable light-responsive release of entrapped dye from vesicles.
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Azacalix[2]arene[2]triazine-based receptors bearing carboxymethyl pendant arms on nitrogen bridges: synthesis and evaluation of their coordination ability towards copper(II)

10 January, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,589-599
DOI: 10.1039/C3OB42047G, PaperJoao M. Caio, Teresa Esteves, Silvia Carvalho, Cristina Moiteiro, Vitor Felix
A series of azacalix[2]arene[2]triazine macrocycles with the four nitrogen bridges functionalized with carboxymethyl pendant arms is reported. The coordination ability of dialkylamine derivatives for copper(II) was evaluated.
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Stereoselective tandem synthesis of thiazolo fused naphthyridines and thienopyridines from o-alkynylaldehydes via Au(III)-catalyzed regioselective 6-endo-dig ring closure

10 January, 2014 - 11:54

Org. Biomol. Chem., 2014, 12,552-556
DOI: 10.1039/C3OB42035C, CommunicationRajeev R. Jha, Rakesh K. Saunthwal, Akhilesh K. Verma
An operationally simple tandem approach for the stereoselective synthesis of thiazolo fused naphthyridines 5a-o and thienopyridines 8a-e is described.
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Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation of (Z)-[small alpha]-Santalol

8 January, 2014 - 11:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42174K, CommunicationHirekodathakallu V Thulasiram, Pankaj P. Daramwar, Prabhakar L. Srivastava, Swati P Kolet
Biocatalyst mediated regio- and stereo-selective hydroxylation and epoxidation on (Z)-[small alpha]-santalol was achieved for the first time, using a fungal strain M. piriformis. Four novel metabolites were characterized as 10,11-cis-[small beta]-epoxy-[small alpha]-santalol, 5[small alpha]-hydroxy-(Z)-[small alpha]-santalol,...
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Site-selected incorporation of 5-carboxymethylaminomethyl(-2-thio)uridine into RNA sequences by phosphoramidite chemistry

8 January, 2014 - 11:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42302F, CommunicationGrazyna Leszczynska, Jakub Pieta, Karolina Wozniak, Andrzej Malkiewicz
5-Carboxymethylaminomethyluridine (cmnm5U) and 5-carboxymethylaminomethyl-2-thiouridine (cmnm5s2U) are located at the wobble position in several cytosolic and mitochondrial tRNA sequences. In this paper, we report the first site-selected incorporation of cmnm5U and...
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Amphiphilic Polyethylenimine (PEI) as High efficient non-viral gene carrier

8 January, 2014 - 11:17
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB42279H, PaperXibo Yan, Yue Zhang, Hongbo Zhang, Peng George Wang, Xin Wang
Efficient and safe gene vectors are important for gene therapy. Here, a novel family amphiphilic polyethylenimine (PEI) LD1-PEI bearing a polar group of branched PEI 25K and four dodecyl chains...
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