Royal Society of Chemistry

Conformational equilibria in selected A-type trimeric procyanidins

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB02086C, PaperMarta K. Dudek (Jamroz), Slawomir Kazmierski, Kamil Stefaniak, Vitold B. Glinski, Jan. A. Glinski
There are two favored conformations of A-type procyanidin trimers: the (+[small phi])-rotamer and the (-[small phi]) one. Their ratio depends on the procyanidin structure and solvent - different solvents favor different conformers.
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Facile diverted synthesis of pyrrolidinyl triazoles using organotrifluoroborate: discovery of potential mPTP blockers

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01967A, PaperOpen Access Open Access Creative Commons Licence&nbsp This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence.Sun hwa Jung, Kihang Choi, Ae Nim Pae, Jae Kyun Lee, Hyunah Choo, Gyochang Keum, Yong Seo Cho, Sun-Joon Min
Pyrrolidinyl triazoles were synthesized via Huisgen 1,3-dipolar cycloadditions of ethynyl trifluoroborate followed by Suzuki-Miyaura coupling reactions and biologically evaluated as potential mPTP blockers.
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Synthesis of nitriles via palladium-catalyzed water shuffling from amides to acetonitrile

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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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Synthesis and LC-MS/MS analysis of desmosine-CH2, a potential internal standard for the degraded elastin biomarker desmosine

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01438C, PaperYuko Murakami, Rina Suzuki, Hiroto Yanuma, Jiangtao He, Shuren Ma, Gerard M. Turino, Yong Y. Lin, Toyonobu Usuki
Chemical synthesis and LC-MS/MS analysis of desmosine-CH2, a potential internal standard for the degraded elastin biomarker desmosine, are achieved.
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Gold-catalyzed carboalkoxylations of 2-ethynylbenzyl ethers to form 1- and 3-substituted 2-methoxy-1-H-indenes: Bronsted acids versus gold catalysis

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01794C, PaperChun-Hao Chen, Chiou-Dong Wang, Yi-Feng Hsieh, Rai-Shung Liu
Selective synthesis of 1- and 3-substituted 2-methoxyindenes from the carboalkoxylations of 2-ethynylbenzyl ethers is described.
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Comparative perspective and synthetic applications of transition metal mediated oxidative cyclisation of 1,5-dienes towards cis-2,5-disubstituted tetrahydrofurans

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01491J, Review ArticleNadeem S. Sheikh
Synthesis of cis-2,5-disubstituted tetrahydrofuran rings from 1,5-diene precursors using metal-oxo species along with their mechanistic proposals and synthetic applications is concisely reviewed.
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Diastereoselective photodimerization reactions of chromone-2-carboxamides to construct a C2-chiral scaffold

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01827C, PaperFumitoshi Yagishita, Nozomi Baba, Yuki Ueda, Satoshi Katabira, Yoshio Kasashima, Takashi Mino, Masami Sakamoto
Irradiation of three chromone-2-carboxamides with a chiral auxiliary resulted in diastereoselective formation of a C2-chiral anti-HH dimer scaffold.
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Design and synthesis of potent hydroxamate inhibitors with increased selectivity within the gelatinase family

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01516A, PaperJose Maria Zapico, Anna Puckowska, Kamila Filipiak, Claire Coderch, Beatriz de Pascual-Teresa, Ana Ramos
Triazole-based inhibitors with high potency and selectivity for MMP-2 were obtained through a click chemistry approach.
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Radical reactions of borohydrides

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01784F, Review ArticleTakuji Kawamoto, Ilhyong Ryu
This review article focuses on state-of-the-art borohydride based radical reactions, also covering earlier work, kinetics and some DFT calculations with respect to the hydrogen transfer mechanism.
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Fischer indolisation of N-([small alpha]-ketoacyl)anthranilic acids into 2-(indol-2-carboxamido)benzoic acids and 2-indolyl-3,1-benzoxazin-4-ones and their NMR study

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01714E, PaperKarel Proisl, Stanislav Kafka, Damijana Urankar, Martin Gazvoda, Roman Kimmel, Janez Kosmrlj
A new approach to 2-indolyl functionalized anthranilic acids and 3,1-benzoxazin-4-ones.
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Carbohydrate-based N-heterocyclic carbenes for enantioselective catalysis

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, 12,9272-9278
DOI: 10.1039/C4OB01852D, PaperGavin 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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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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The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

Org. Biomol. Chem., 2014, Advance Article
DOI: 10.1039/C4OB01811G, PaperDebendra K. Mohapatra, D. Sai Reddy, N. Arjunreddy Mallampudi, Janardhan Gaddam, Sowjanya Polepalli, Nishant Jain, J. S. Yadav
A convergent and concise total synthesis of zeaenol, 7-epi-zeaenol, and its analogues is achieved using protecting group-directed NHK reaction.
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Oxidative nucleophilic strategy for synthesis of thiocyanates and trifluoromethyl sulfides from thiols

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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

Org. and Biomol. Chem. - 30 October, 2014 - 10:54

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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