Org. and Biomol. Chem.

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Understanding the polar mechanism of the ene reaction. A DFT study

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01279H, PaperLuis R. Domingo, Maria J. Aurell, Patricia Perez
A good correlation between the activation energy and global electron density transfer at the transition structure of ene reactions has been found. The proposed polar mechanism can be easily predicted analysing the electrophilicity/nucleophilicity indices of the reagents.
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Modulation of DNA-polyamide interaction by [small beta]-alanine substitutions: a study of positional effects on binding affinity, kinetics and thermodynamics

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01456A, PaperShuo Wang, Karl Aston, Kevin J. Koeller, G. Davis Harris, Nigam P. Rath, James K. Bashkin, W. David Wilson
The substitution of an internal pyrrole with a [small beta] motif has large and diverse effects on hairpin polyamide-DNA binding affinity, kinetics and binding orientation.
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Development and mechanistic studies of an optimized receptor for trimethyllysine using iterative redesign by dynamic combinatorial chemistry

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,7059-7067
DOI: 10.1039/C4OB01249F, PaperNicholas K. Pinkin, Marcey L. Waters
Iterative monomer redesign leads to a Kme3-peptide receptor with 10-fold tighter affinity and 5-fold improved selectivity over Kme2 than the original receptor. Thermodynamic analysis provides insight into this improvement.
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Novel ruthenium-catalyst for hydroesterification of olefins with formates

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,6972-6976
DOI: 10.1039/C4OB01246A, CommunicationIrina Profir, Matthias Beller, Ivana Fleischer
A new catalyst based on a bidentate P,N-ligand and ruthenium dodecacarbonyl for the hydroesterification of olefins with formates is reported.
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Silver triflate and triflic anhydride-promoted expedient synthesis of acylated 1-aminoisoquinolines

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,6982-6985
DOI: 10.1039/C4OB01301H, CommunicationYuewen Li, Liang Gao, Hui Zhu, Guangming Li, Zhiyuan Chen
A practical and convergent synthesis of biologically active 1-(N-acyl)-1-aminoisoquinolines from the reaction of 2-alkynylbenzaldoximes with amides has been realized.
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A facile manganese dioxide mediated oxidation of primary benzylamines to benzamides

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,7150-7158
DOI: 10.1039/C4OB01166J, PaperA. Poeschl, D. M. Mountford
An efficient and high yielding manganese dioxide mediated oxidation of benzylamines to the corresponding amides under mild reaction conditions.
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Developing principles for predicting ionic liquid effects on reaction outcome. A demonstration using a simple condensation reaction

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,7092-7099
DOI: 10.1039/C4OB01070A, PaperSinead T. Keaveney, Karin S. Schaffarczyk McHale, Ronald S. Haines, Jason B. Harper
Predictions of the effects of the proportion and the components of an ionic liquid on the reaction rate are shown to correlate well with experimental results.
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A convenient tandem one-pot synthesis of donor-acceptor-type triphenylene 2,3-dicarboxylic esters from diarylacetylene

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,6977-6981
DOI: 10.1039/C4OB01503G, CommunicationChun Feng, Xian-Li Tian, Jing Zhou, Shi-Kai Xiang, Wen-Hao Yu, Bi-Qin Wang, Ping Hu, Carl Redshaw, Ke-Qing Zhao
An efficient one-pot synthetic procedure was developed for the direct preparation of polysubstituted triphenylene 2,3-dicarboxylic esters via a tandem addition process from diarylacetylene.
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Short asymmetric synthesis of phenanthroindolizidines through chiral homoallylic sulfinamines

30 August, 2014 - 20:54

Org. Biomol. Chem., 2014, 12,7018-7025
DOI: 10.1039/C4OB01133C, PaperCintia Anton-Torrecillas, Jose C. Gonzalez-Gomez
An expeditious synthesis of enantioenriched phenanthroindolizidines has been achieved using tert-butylsulfinamide as a chiral inductor and without any other protecting group.
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Switchable regioselectivity in the PIFA-BF3[middle dot]Et2O mediated oxidative coupling of meso-brominated Ni(II) porphyrin

28 August, 2014 - 20:17

Org. Biomol. Chem., 2014, 12,6990-6993
DOI: 10.1039/C4OB01517G, CommunicationChuan-Mi Feng, Yi-Zhou Zhu, Yun Zang, Yu-Zhang Tong, Jian-Yu Zheng
A simple and efficient method has been developed for the switchable synthesis of directly linked meso-brominated Ni(II) porphyrin dimers through PIFA-BF3[middle dot]Et2O mediated oxidative coupling.
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Removal of amino groups from anilines through diazonium salt-based reactions

28 August, 2014 - 20:17

Org. Biomol. Chem., 2014, 12,6965-6971
DOI: 10.1039/C4OB01286K, Review ArticleLinman He, Guanyinsheng Qiu, Yueqiu Gao, Jie Wu
In situ generation of diazonium salts from anilines represents an efficient and practical pathway, leading to a series of useful structures. The amino group in anilines acts as a formal leaving group in various coupling reactions.
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Evolution of a strategy for preparing bioactive small molecules by sequential multicomponent assembly processes, cyclizations, and diversification

26 August, 2014 - 19:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB00835A, Review ArticleJames J. Sahn, Brett A. Granger, Stephen F. Martin
Multicomponent assembly processes are key steps in the synthesis of diverse polycyclic heterocycles with a broad array of biological activities.
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9-amino-(9-deoxy)cinchona alkaloid-derived new chiral phase-transfer catalysts

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01648C, PaperWenwen Peng, Jingwei Wan, xuebing ma, Bing Xie
A new class of 9-amino-(9-deoxy) cinchona alkaloid-derived chiral phase-transfer catalysts bearing amino groups was developed by using the known cinchona alkaloids as starting materials. Due to the transformation of 9-hydroxyl...
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A Lewis acid-mediated conformational switch

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01556H, PaperPeter Clarke Knipe, Hannah Lingard, Ian M Jones, Sam Thompson, Andrew D Hamilton
Molecules that change conformation in response to a stimulus have numerous uses, such as artificial chemoreceptors, novel drug delivery strategies and liquid crystal technology. Here we describe the design, synthesis...
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Neither azeotropic drying, nor base, nor other additives - a minimalist approach to 18F-labeling

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01336K, PaperRaphael Richarz, Philipp Krapf, Elizaveta Alexandrovna Urusova, Bernd Neumaier, Boris Dmitrievitch Zlatopolskiy
A novel, efficient, time-saving and reliable radiolabeling procedure via nucleophilic substitution with [18F]fluoride is described. Different radiolabeled aliphatic and aromatic compounds were prepared in high radiochemical yields simply by the...
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Origins of exo-Stereoselectivity of Norbornene in Hetero Diels-Alder Reactions

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01217H, PaperSesil Agopcan, Selami Ercan, Sule Erol, Ilknur Dogan, Viktorya Aviyente
In this study the exo selectivity in the hetero Diels-Alder reaction of atropisomeric 5-benzylidine-2-arylimino-3-aryl-thiazolidine-4-thiones with norbornene has been investigated with computational tools. Taking into account the M/P chiral character of...
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Non-isoprenoid Polyene Natural Products - Structures and Synthetic Strategies

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01337A, Review ArticleAndrew Whiting, Katrina Madden, Fathia Mosa
This review provides insight into the variety of structures and biological activities found in the non-isoprenoid family of polyene natural products and examines the strategies and synthetic methods applied for...
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Enantioselective aza-Morita-Baylis-Hillman reaction between acrylates and N-Boc isatin ketimines: asymmetric construction of chiral 3-substituted-3-aminooxindoles

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01358A, PaperXuan Zhao, Tian-Ze Li, Jing-Ying Qian, Feng Sha, Xin-Yan Wu
The first enantioselective aza-Morita-Baylis-Hillman reaction of acrylates with ketimines derived from isatins has been developed. With 2 mol% of chiral bifunctional phosphine-squaramide 4e, optically active 3-substituted-3-amino-2-oxindoles were obtained in excellent...
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Mechanisms for enzymatic cleavage of the N-glycosidic bond in DNA

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01063A, Review ArticleAlexander Drohat, Atanu Maiti
DNA glycosylases remove damaged or enzymatically modified nucleobases from DNA, thereby initiating the base excision repair (BER) pathway, which is found in all forms of life. These ubiquitous enzymes promote...
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A Small Synthetic Molecule Forms Selective Potassium Channels to Regulate Cell Membrane Potential and Blood Vessel Tone

26 August, 2014 - 19:54
Org. Biomol. Chem., 2014, Accepted Manuscript
DOI: 10.1039/C4OB01420K, PaperD Yang, Hui-Yan Zha, Bing Shen, Kwok-Hei Yau, Shing-To Li, Xiao-Qiang Yao
In living cell membranes, K+ permeability is higher than other ions such as Na+ and Cl- owing to abundantly expressed K+ channels. Polarized membrane potential is mainly established by K+...
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