Org. and Biomol. Chem.

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Fe-promoted radical cyanomethylation/arylation of arylacrylamides to access oxindoles via cleavage of the sp3 C-H of acetonitrile and the sp2 C-H of phenyl group

9 November, 2014 - 13:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02172J, CommunicationChengjian Zhu, Changduo Pan, Honglin Zhang
Radical cyanomethylation/arylation of arylacrylamides to access oxindoles by acetonitrile as the radical precursor is discribed. This reaction involved dual C-H bonds functionalization, including the sp3 C-H of acetonitrile and the...
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Enantioselective Total Synthesis of Sch-725674

7 November, 2014 - 12:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02136C, PaperKrishna P Kaliappan, Kota Ramakrishna
An enantioselective total synthesis of Sch-725674, a unique 14-membered macrolactone, has been accomplished in 13 steps. The step-wise dithiane alkylation served as a strategic step to assemble the northern and...
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Kinetic evaluation of glucose 1-phosphate analogues with a thymidylyltransferase using a continuous coupled enzyme assay

7 November, 2014 - 12:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02057J, PaperStephanie M. Forget, Alison Jee, Deborah A Smithen, Rajendra Jagdhane, Stephen A Beaton, Raymond T Syvitski, David RJ Palmer, David L Jakeman
Cps2L, a thymidylytransferase, is the first enzyme in Streptococcus pneumoniae L-rhamnose biosynthesis and an antibacterial target. We herein report the evaluation of six sugar phosphate analogues selected to further probe...
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Rhodium(II)-Catalyzed Intramolecular Formal [4+3] Cycloadditions of Dienyltriazoles: Rapid Access to Fused 2,5-Dihydroazepines

7 November, 2014 - 12:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01910E, PaperYefeng Tang, Yu Tian, Yuanhao Wang, Hai Shang, Xudong Xu
Rhodium(II)-catalyzed intramolecular [4+3] cycloadditions of dienyltriazoles have been developed, which enable the efficient synthesis of various fused 2,5-dihydroazepines. Mechanistically, the titled reaction proceeds via an interesting tandem cyclopropanation/aza-Cope rearrangement.
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Developing a Targeting System for Bacterial Membranes: Measuring Receptor-Phosphatidylglycerol Interactions with 1H NMR, ITC, and Fluorescence Correlation Spectroscopy

5 November, 2014 - 12:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01895H, PaperAmanda Alliband, Zifan Wang, Christopher Thacker, Douglas S. English, Dennis Huntington Burns
An ammonium picket porphyrin that targets bacterial membranes has been prepared and shown to bind to phosphatidylglycerol (PG), a bacterial lipid, when the lipid was in solution, contained within synthetic...
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Systematic methodology for the development of biocatalytic hydrogen-borrowing cascades: Application to the synthesis of chiral [small alpha]-substituted carboxylic acids from [small alpha]-substituted [small alpha]-[small beta] unsaturated aldehydes.

5 November, 2014 - 12:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB02282C, PaperTanja Knaus, Francesco G Mutti, Luke Humphreys, Nicholas J Turner, Nigel S Scrutton
Ene-reductases (ERs) are flavin dependent enzymes that catalyze the asymmetric reduction of activated carbon-carbon double bonds. In particular, [small alpha]-[small beta] unsaturated carbonyl compounds (e.g. enals and enones) as well as nitroalkanes...
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L-Valine Derived Chiral N-Sulfinamides as Effective Organocatalysts for the Asymmetric Hydrosilylation of N-Alkyl and N-Aryl Protected Ketimines

5 November, 2014 - 12:17
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01257G, PaperChao Wang, Li Zhou, Jian Sun, Xinjun Wu
L-Valine derived N-sulfinamides have been developed as efficient enantioselective Lewis basic organocatalysts for the asymmetric reduction of N-aryl and N-alkyl ketimines with trichlorosilane. Catalyst 3c afforded up to 99% yield...
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Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9109-9112
DOI: 10.1039/C4OB01825G, CommunicationWandi Zhang, Christopher W. Haskins, Yang Yang, Mingji Dai
Palladium-catalyzed synthesis of nitriles from amides has been described.
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Unusual (Z)-selective palladium(II)-catalysed addition of aryl boronic acids to vinylaziridines

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9113-9115
DOI: 10.1039/C4OB01786B, CommunicationJieXiang Yin, Theresa Mekelburg, Christopher Hyland
The palladium(II)-catalysed addition of arylboronic acids to vinylaziridines has been developed. This reaction proceeds via an insertion/ring-opening process to provide (E)-allylsulfonamides. This stereoselectivity is complimentary to existing methods that typically proceed via an SN2[prime or minute] mechanism to yield (Z)-allylic systems.
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Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9180-9183
DOI: 10.1039/C4OB02056A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Alexander S. Henderson, John F. Bower, M. Carmen Galan
Versatile syntheses of C2-linked and C2-symmetric carbohydrate-based NHC[middle dot]HCls from functionalised amino-carbohydrate derivatives are reported. The corresponding Rh complexes were evaluated in asymmetric hydrosilylation of ketones.
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RhIII-catalyzed dual directing group assisted sterically hindered C-H bond activation: a unique route to meta and ortho substituted benzofurans

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9105-9108
DOI: 10.1039/C4OB01876A, CommunicationChien-Hung Yeh, Wei-Chen Chen, Parthasarathy Gandeepan, Ya-Chun Hong, Cheng-Hung Shih, Chien-Hong Cheng
A new strategy for the synthesis of highly substituted benzofurans from meta-substituted hydroxybenzenes and alkynes via a rhodium(III)-catalyzed activation of a sterically hindered C-H bond is demonstrated.
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Sialylation of lactosyl lipids in membrane microdomains by T. cruzi trans-sialidase

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9272-9278
DOI: 10.1039/C4OB01852D, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Gavin T. Noble, Faye L. Craven, Maria Dolores Segarra-Maset, Juana Elizabeth Reyes Martinez, Robert Sardzik, Sabine L. Flitsch, Simon J. Webb
Soluble T. cruzi trans-sialidase transformed a synthetic lactosyl glycolipid in microdomains more slowly than the same substrate dispersed across the bilayer surface, producing phospholipid vesicles with a Neu5Ac([small alpha]2-3)Gal([small beta]1-4)Glc "glycocalyx".
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A highly enantioselective and regioselective organocatalytic direct Mannich reaction of methyl alkyl ketones with cyclic imines benzo[e][1,2,3]oxathiazine 2,2-dioxides

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9101-9104
DOI: 10.1039/C4OB01902D, CommunicationYou-Qing Wang, Xiao-Yu Cui, Yuan-Yuan Ren, Yongna Zhang
A specific regioselective direct Mannich reaction of methyl alkyl ketones with cyclic imines benzo[e][1,2,3]oxathiazine 2,2-dioxides is realized with 87-97% ee.
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Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9200-9206
DOI: 10.1039/C4OB01655F, PaperKazuya Yamaguchi, Konomi Sakagami, Yumi Miyamoto, Xiongjie Jin, Noritaka Mizuno
In the presence of a 2 [times] 2 manganese oxide-based octahedral molecular sieve (OMS-2) and potassium fluoride (KF), various thiocyanates and trifluoromethyl sulfides could be synthesized from thiols in almost quantitative yields.
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The asymmetric syntheses of pyrrolizidines, indolizidines and quinolizidines via two sequential tandem ring-closure/N-debenzylation processes

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9223-9235
DOI: 10.1039/C4OB01737D, PaperStephen G. Davies, Ai M. Fletcher, Emma M. Foster, Ian T. T. Houlsby, Paul M. Roberts, Thomas M. Schofield, James E. Thomson
Asymmetric syntheses of (-)-lupinine (n = m = 1), (+)-isoretronecanol (n = m = 0), (+)-5-epi-tashiromine (n = 0, m = 1) and the azabicyclic core within stellettamides A-C (n = 1, m = 0) were achieved in 8 steps or fewer.
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One molecule of ionic liquid and tert-alcohol on a polystyrene-support as catalysts for efficient nucleophilic substitution including fluorination

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9264-9271
DOI: 10.1039/C4OB01781A, PaperSandip S. Shinde, Sunil N. Patil
The tert-alcohol and ionic liquid solvents in one molecule [mim-tOH][OMs] was immobilized on polystyrene and reported to be a highly efficient catalyst in aliphatic nucleophilic substitution using alkali metal salts.
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Catalyst-free reductive amination of aromatic aldehydes with ammonium formate and Hantzsch ester

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9092-9096
DOI: 10.1039/C4OB01590H, CommunicationPan-Pan Zhao, Xin-Feng Zhou, Jian-Jun Dai, Hua-Jian Xu
Both symmetric and asymmetric aromatic secondary amines were obtained with ammonium formate and Hantzsch ester in the developed protocol.
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TBHP-promoted sequential carboxamidation and aromatisation of aryl isonitriles with formamides

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9257-9263
DOI: 10.1039/C4OB01850H, PaperXiaomei Feng, Hui Zhu, Lei Wang, Yan Jiang, Jiang Cheng, Jin-Tao Yu
The tert-butyl hydroperoxide (TBHP)-promoted sequential carboxamidation and aromatisation of isonitriles with formamides was developed. This reaction involved the addition of formamide radicals to isonitriles and sequential C-C bond formation by intramolecular aromatic cyclisation.
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Organocatalytic enantioselective [small alpha]-amination of 5-substituted rhodanines: an efficient approach to chiral N,S-acetals

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9097-9100
DOI: 10.1039/C4OB01921K, CommunicationHuanrui Zhang, Baomin Wang, Longchen Cui, Ying Li, Jingping Qu, Yuming Song
A highly efficient approach to chiral N,S-acetals by asymmetric amination of 5-substituted rhodanines catalyzed by quinine or quinidine is developed.
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2-Alkynylbenzaldoxime: a versatile building block for the generation of N-heterocycles

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9045-9053
DOI: 10.1039/C4OB01618A, Review ArticleLinman He, Hongming Nie, Guanyinsheng Qiu, Yueqiu Gao, Jie Wu
Recent advancement in the generation of N-heterocycles starting from 2-alkynylbenzaldoximes via tandem reactions is described based on different reaction types.
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