Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Copper(I)-induced amplification of a [2]catenane in a virtual dynamic library of macrocyclic alkenes

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6167-6174
DOI: 10.1039/C4OB01009D, PaperJose Augusto Berrocal, Marko M. L. Nieuwenhuizen, Luigi Mandolini, E. W. Meijer, Stefano Di Stefano
The interlocked virtual component 1 of a well-behaved dynamic library of cyclic olefins is resuscitated by means of the template effect.
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Highly enantioselective synthesis of bisoxindoles with two vicinal quaternary stereocenters via Lewis base mediated addition of oxindoles to isatin-derived ketimines

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6085-6088
DOI: 10.1039/C4OB01039F, CommunicationZhongkai Tang, Yan Shi, Haibin Mao, Xuebin Zhu, Weipeng Li, Yixiang Cheng, Wen-Hua Zheng, Chengjian Zhu
A highly efficient method provides access to the bisoxindole structure moiety with two vicinal quaternary stereogenic centers (>99 : 1 dr, >99% ee).
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Convergent chemoenzymatic synthesis of a library of glycosylated analogues of pramlintide: structure-activity relationships for amylin receptor agonism

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01208A, PaperRenata Kowalczyk, Margaret A. Brimble, Yusuke Tomabechi, Antony J. Fairbanks, Madeleine Fletcher, Debbie L. Hay
The synthesis of a library of N-glycosylated pramlintide analogues to establish the SAR of amylin receptor agonism has been undertaken.
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Fluorous chiral bisoxazolines: application in copper-catalyzed asymmetric [small alpha]-hydrophosphonylation

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5843-5846
DOI: 10.1039/C4OB01144A, CommunicationTao Deng, Hongjun Wang, Chun Cai
A copper-catalyzed asymmetric [small alpha]-hydrophosphonylation of isatins with a novel fluorous bis(oxazoline) as a ligand is presented.
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A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines via dual C(sp3)-H/C(sp2)-H functionalizations

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5839-5842
DOI: 10.1039/C4OB01256A, CommunicationZhi-Qiang Zhu, Tian-Tian Wang, Peng Bai, Zhi-Zhen Huang
A cascade alkylarylation reaction of 2-isocyanobiphenyls with simple alkanes for 6-alkyl phenanthridines has been developed through dual C(sp3)-H/C(sp2)-H functionalizations.
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Syntheses and characterization of liposome-incorporated adamantyl aminoguanidines

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6005-6013
DOI: 10.1039/C4OB00592A, PaperMarina Sekutor, Adela Stimac, Kata Mlinaric-Majerski, Ruza Frkanec
A series of mono and bis-aminoguanidinium adamantane derivatives has been synthesized and incorporated into liposomes.
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Studies on copper(I)-catalyzed highly regio- and stereo-selective hydroboration of alkynamides

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5945-5953
DOI: 10.1039/C4OB00979G, PaperGuangke He, Shan Chen, Qiang Wang, Hai Huang, Qijun Zhang, Dongming Zhang, Rong Zhang, Hongjun Zhu
The regio-selectivity of the Cu(I)-catalyzed hydroboration of N-(1-alkynyl)amides is unexpectedly opposite to that in the carbometallation reaction of alkynamides.
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Solid-phase synthesis of peptoid-like oligomers containing diverse diketopiperazine units

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5831-5834
DOI: 10.1039/C4OB00829D, CommunicationSujit Suwal, Thomas Kodadek
An efficient protocol for the solid-phase synthesis of diverse diketopiperazines is reported.
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Mutation of Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase at Trp-110 affects stereoselectivity of aromatic ketone reduction

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5905-5910
DOI: 10.1039/C4OB00794H, PaperJay M. Patel, Musa M. Musa, Luis Rodriguez, Dewey A. Sutton, Vladimir V. Popik, Robert S. Phillips
Secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus was mutated at Trp-110, and mutant enzymes with high activity and high stereoselectivity for aromatic ketone reduction were identified.
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Breaking the dichotomy of reactivity vs. chemoselectivity in catalytic SN1 reactions of alcohols

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5990-5994
DOI: 10.1039/C4OB01265H, PaperMalik Hellal, Florian C. Falk, Elena Wolf, Marian Dryzhakov, Joseph Moran
B(C6F5)3 possesses a different reactivity/chemoselectivity profile than traditional Lewis and Bronsted acids and is effective at enabling catalytic SN1 reactions of alcohols in the presence of acid sensitive groups without compromising reaction rates, substrate scope or catalyst loadings.
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Enantioselective palladium catalyzed conjugate additions of ortho-substituted arylboronic acids to [small beta],[small beta]-disubstituted cyclic enones: total synthesis of herbertenediol, enokipodin A and enokipodin B

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5883-5890
DOI: 10.1039/C4OB01085J, PaperJeffrey Buter, Renee Moezelaar, Adriaan J. Minnaard
Palladium catalyzed asymmetric conjugate addition of ortho-substituted arylboronic acids to cyclic enones and its application in natural product synthesis.
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Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5995-6004
DOI: 10.1039/C4OB00830H, PaperXiaoli Wang, Linna Wang, Xiao Sheng, Zhangjian Huang, Tingting Li, Ming Zhang, Jinyi Xu, Hui Ji, Jian Yin, Yihua Zhang
Compound 8e protected against the collagen and adrenaline induced thrombosis in mice, and exhibited greater antithrombotic activity than NBP and aspirin in rats.
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C 3-Symmetric chiral trisimidazoline-catalyzed Friedel-Crafts (FC)-type reaction

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,5827-5830
DOI: 10.1039/C4OB00925H, CommunicationShinobu Takizawa, Shuichi Hirata, Kenichi Murai, Hiromichi Fujioka, Hiroaki Sasai
The first imidazoline-catalyzed enantioselective Friedel-Crafts (FC)-type reaction was established using C3-symmetric chiral trisimidazolines.
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Catalytic asymmetric nucleophilic openings of 3-substituted oxetanes

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6028-6032
DOI: 10.1039/C4OB00920G, PerspectiveZhaobin Wang, Zhilong Chen, Jianwei Sun
Important progress has been made in catalytic asymmetric ring-opening of 3-substituted oxetanes, but significant challenges and opportunities remain.
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One-pot pseudo three-component reaction of nitroketene-N,S-acetals and aldehydes for synthesis of highly functionalized hexa-substituted 1,4-dihydropyridines

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6223-6238
DOI: 10.1039/C4OB00628C, PaperH. Surya Prakash Rao, A. Parthiban
Pseudo three-component condensation of aliphatic/aromatic/[small alpha],[small beta]-unsaturated aldehydes and nitroketene-N,S-acetals to afford diversely functionalized hexa-substituted 1,4-dihydropyridines under 2-aminopyridine catalysis was achieved.
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CuI-catalyzed cross-coupling of terminal alkynes with dialkoxycarbenes: a general method for the synthesis of unsymmetrical propargylic acetals

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6215-6222
DOI: 10.1039/C4OB00614C, PaperTiebo Xiao, Ping Zhang, Yang Xie, Jun Wang, Lei Zhou
A general source of dialkoxycarbenes, 2,2-dialkoxy-5,5-dimethyl-[capital Delta]3-1,3,4-oxadiazolines, have been successfully employed as coupling partners in CuI-catalyzed cross-coupling reactions with terminal alkynes, which afforded various unsymmetrical propargylic acetals in good yields.
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Organic synthetic transformations using organic dyes as photoredox catalysts

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6059-6071
DOI: 10.1039/C4OB00843J, Review ArticleOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Shunichi Fukuzumi, Kei Ohkubo
This review article presents various photocatalytic transformation such as oxygenation, halogenation and C-C bond formation with organic photoredox catalysts.
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From in vitro to in cellulo: structure-activity relationship of (2-nitrophenyl)methanol derivatives as inhibitors of PqsD in Pseudomonas aeruginosa

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6094-6104
DOI: 10.1039/C4OB00707G, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Michael P. Storz, Giuseppe Allegretta, Benjamin Kirsch, Martin Empting, Rolf W. Hartmann
More than 60 derivatives of (2-nitrophenyl)methanol were synthesized and evaluated regarding their potency to inhibit PqsD. In vitro and in cellulo structure-activity relationships were derived.
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Catalytic functionalization of tertiary alcohols to fully substituted carbon centres

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6033-6048
DOI: 10.1039/C4OB00718B, Review ArticleLong Chen, Xiao-Ping Yin, Cui-Hong Wang, Jian Zhou
This review summarizes the recent progresses in the catalytic nucleophilic substitution of tertiary alcohols using carbon or heteroatom based nucleophiles for the efficient, diverse and atom economical construction of fully substituted carbon centres, and discusses synthetic opportunities that are still open.
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Recent advances in the synthesis of nitroolefin compounds

29 July, 2014 - 11:17

Org. Biomol. Chem., 2014, 12,6049-6058
DOI: 10.1039/C4OB00573B, Review ArticleGuobing Yan, Arun Jyoti Borah, Lianggui Wang
This review focuses on recent achievements in nitroolefin synthesis and the mechanisms of the reactions are also discussed.
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