Org. and Biomol. Chem.

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RSC - Org. Biomol. Chem. latest articles
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Direct conversion of allyl arenes to aryl ethylketones via a TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5613-5616
DOI: 10.1039/C5OB00586H, CommunicationJinWu Zhao, Li Liu, ShiJian Xiang, Qiang Liu, HuoJi Chen
A TBHP-mediated palladium-catalyzed tandem isomerization-Wacker oxidation of terminal alkenes was developed.
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Palladium-catalyzed asymmetric allylic amination of racemic butadiene monoxide with isatin derivatives

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5826-5830
DOI: 10.1039/C5OB00663E, PaperGen Li, Xiangqing Feng, Haifeng Du
Pd-catalyzed asymmetric aminations of butadiene monoxide with isatin derivatives using P/alkene ligands gave high yields, ees and regioselectivity ratios.
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Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5793-5803
DOI: 10.1039/C5OB00541H, PaperAli H. Essa, Reinner I. Lerrick, Ece Ciftci, Ross W. Harrington, Paul G. Waddell, William Clegg, Michael J. Hall
2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations.
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Tri- and tetra-substituted cyclen based lanthanide(III) ion complexes as ribonuclease mimics: a study into the effect of log Ka, hydration and hydrophobicity on phosphodiester hydrolysis of the RNA-model 2-hydroxypropyl-4-nitrophenyl phosphate (HPNP)

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5804-5816
DOI: 10.1039/C4OB02384F, PaperAnn-Marie Fanning, Sally. E. Plush, Thorfinnur Gunnlaugsson
Lanthanide(III) complexes of 'pseudo' dipeptide ligands and 3'-pyridine ligands have been characterised as metallo-ribonuclease mimics.
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Direct synthesis of a geminal zwitterionic phosphonium/hydridoborate system - developing an alternative tool for generating frustrated Lewis pair hydrogen activation systems

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5783-5792
DOI: 10.1039/C5OB00634A, PaperJiangang Yu, Gerald Kehr, Constantin G. Daniliuc, Christoph Bannwarth, Stefan Grimme, Gerhard Erker
A convenient way to a new class of geminal Mes2PH+/B(C6F5)2H- pairs is presented.
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Simultaneous introduction of trifluoromethyl and [small lambda]6-pentafluorosulfanyl substituents using F5S-C[triple bond, length as m-dash]C-CF3 as a dienophile

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5625-5628
DOI: 10.1039/C5OB00610D, CommunicationBlazej Duda, Dieter Lentz
SF5-C[triple bond, length as m-dash]C-CF3 as a powerful dienophile in Diels-Alder reactions, provides the corresponding products in up to quantitative yields and allows the introduction of the pentafluorosulfanyl group and trifluoromethyl group at the 1,2 position.
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Fluorine containing amino acids: synthesis and peptide coupling of amino acids containing the all-cis tetrafluorocyclohexyl motif

20 May, 2015 - 13:17

Org. Biomol. Chem., 2015, 13,5621-5624
DOI: 10.1039/C5OB00650C, CommunicationMohammed Salah Ayoup, David B. Cordes, Alexandra M. Z. Slawin, David O'Hagan
A synthesis of amino acids carrying the all-cis tetrafluorocyclohexyl ring moiety is demonstrated and protection/deprotection elaborations are illustrated which show that this facially polarised ring motif may be incorporated into peptides.
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Binaphthyl-1,2,3-triazole peptidomimetics with activity against Clostridium difficile and other pathogenic bacteria

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5743-5756
DOI: 10.1039/C5OB00576K, PaperSteven M. Wales, Katherine A. Hammer, Amy M. King, Andrew J. Tague, Dena Lyras, Thomas V. Riley, Paul A. Keller, Stephen G. Pyne
Designed binaphthyl-based, cationic peptidomimetic antimicrobials targeting C. difficile, incorporating a click-derived 1,2,3-triazole ester isostere at the C-terminus MICs of 4 [small mu ]g mL-1 against three human isolates of C. difficile.
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Synthetic studies toward the brasilinolides: controlled assembly of a protected C1-C38 polyol based on fragment union by complex aldol reactions

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5716-5733
DOI: 10.1039/C5OB00498E, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.Ian Paterson, Michael P. Housden, Christopher J. Cordier, Paul M. Burton, Friedrich A. Muhlthau, Olivier Loiseleur
A modular strategy for the synthesis of the immunosuppressant macrolide brasilinolide A was adopted based on coupling suitable northern and southern fragments.
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Copper-catalyzed aerobic oxidative amination of C(sp3)-H bonds: synthesis of imidazo[1,5-a]pyridines

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5602-5607
DOI: 10.1039/C5OB00381D, CommunicationDarapaneni Chandra Mohan, Sadu Nageswara Rao, Chitrakar Ravi, Subbarayappa Adimurthy
Copper-catalyzed synthesis of imidazo[1,5-a]pyridine-1-carboxylates through oxidative amination of C(sp3)-H bonds under mild aerobic conditions with broad substrate scope has been achieved.
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A preorganized [small beta]-amino acid bearing a guanidinium side chain and its use in cell-penetrating peptides

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5617-5620
DOI: 10.1039/C5OB00389J, CommunicationYosuke Demizu, Makoto Oba, Koyo Okitsu, Hiroko Yamashita, Takashi Misawa, Masakazu Tanaka, Masaaki Kurihara, Samuel H. Gellman
A cyclic [small beta]-amino acid (APCGu) bearing a side-chain guanidinium group has been developed.
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High solid-state luminescence in propeller-shaped AIE-active pyridine-ketoiminate-boron complexes

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5775-5782
DOI: 10.1039/C5OB00607D, PaperYanping Wu, Zhenyu Li, Qingsong Liu, Xiaoqing Wang, Hui Yan, Shuwen Gong, Zhipeng Liu, Weijiang He
Two pyridine-ketoiminate-based organoboron complexes were demonstrated to possess aggregation-induced emission, large Stokes shift and high quantum yield in the solid-state, which were rationalized through X-ray crystal analysis and electronic structure calculations.
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Indium-catalyzed oxidative cross-dehydrogenative coupling of chromenes with 1,3-dicarbonyls and aryl rings

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5710-5715
DOI: 10.1039/C5OB00277J, PaperFanmei Li, Zhilin Meng, Jing Hua, Wei Li, Hongxiang Lou, Lei Liu
An efficient indium-catalyzed oxidative cross-dehydrogenative coupling of chromenes with 1,3-dicarbonyls and aryl rings promoted by DDQ was described.
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Organocatalytic regioselective asymmetric Michael addition of azlactones to o-hydroxy chalcone derivatives

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5698-5709
DOI: 10.1039/C5OB00121H, PaperShao-Yun Zhang, Gui-Yu Ruan, Zhi-Cong Geng, Nai-Kai Li, Ming Lv, Yong Wang, Xing-Wang Wang
Regio- and enantio-selective Michael addition between azlactones with o-hydroxy chalcone derivatives is reported. Optically active N,O-aminals are obtained in good yields with good to excellent diastereo- and enantio-selectivities.
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Stereoselective construction of functionalized tetracyclic and pentacyclic coumarinopyranpyrazole/pyrimidinedione/coumarin scaffolds using a solid-state melt reaction

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5597-5601
DOI: 10.1039/C5OB00442J, CommunicationManickam Bakthadoss, Damodharan Kannan, Nagappan Sivakumar, Palani Malathi, Vasudevan Manikandan
An assembly of tetra / pentacyclic hybrid scaffolds have been synthesized for the first time using a solid-state melt reaction in a stereoselective fashion with excellent yields.
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Resveratrol-based benzoselenophenes with an enhanced antioxidant and chain breaking capacity

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5757-5764
DOI: 10.1039/C5OB00193E, PaperDamiano Tanini, Lucia Panzella, Riccardo Amorati, Antonella Capperucci, Elio Pizzo, Alessandra Napolitano, Stefano Menichetti, Marco d'Ischia
One-pot selenenylation of resveratrol with Se(0) and SO2Cl2 leads to benzoselenophene derivatives with efficient Trolox-like antioxidant and chain breaking capacity.
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Synthesis of new carolacton derivatives and their activity against biofilms of oral bacteria

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5765-5774
DOI: 10.1039/C5OB00460H, PaperN. Stumpp, P. Premnath, T. Schmidt, J. Ammermann, G. Drager, M. Reck, R. Jansen, M. Stiesch, I. Wagner-Dobler, A. Kirschning
Carolacton, a secondary metabolite isolated from the extracts of Sorangium cellulosum, causes membrane damage and cell death in biofilms of different oral bacteria.
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Galacto configured N-aminoaziridines: a new type of irreversible inhibitor of [small beta]-galactosidases

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5690-5697
DOI: 10.1039/C5OB00532A, PaperAnna Alcaide, Ana Trapero, Yolanda Perez, Amadeu Llebaria
N-Aminoaziridines are potent irreversible inhibitors of galactosidases.
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Heteroatom-substituted tetra(3,4-pyrido)porphyrazines: a stride toward near-infrared-absorbing macrocycles

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5608-5612
DOI: 10.1039/C5OB00651A, CommunicationLenka Vachova, Miloslav Machacek, Radim Kucera, Jiri Demuth, Pavel Cermak, Kamil Kopecky, Miroslav Miletin, Adela Jedlickova, Tomas Simunek, Veronika Novakova, Petr Zimcik
Synthesis and photophysical properties are reported for substituted tetra(3,4-pyrido)porphyrazines that absorb light as far as at 800 nm.
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Enantioselective synthesis of chiral heterocycles containing both chroman and pyrazolone derivatives catalysed by a chiral squaramide

18 May, 2015 - 12:54

Org. Biomol. Chem., 2015, 13,5636-5645
DOI: 10.1039/C4OB02653E, PaperJun-Hua Li, Da-Ming Du
An efficient chiral squaramide-catalysed enantioselective Michael addition of pyrazolin-5-ones to 3-nitro-2H-chromenes afforded chiral heterocycles containing both chroman and pyrazolone derivatives in high to excellent yields (up to 98%) with high enantioselectivities (up to 96%) under very low catalyst loading (0.2 mol%).
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