Org. and Biomol. Chem.

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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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Lewis acid promoted construction of chromen-4-one and isoflavone scaffolds via regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9216-9222
DOI: 10.1039/C4OB01743A, PaperTanmoy Chanda, Sushobhan Chowdhury, Suvajit Koley, Namrata Anand, Maya Shankar Singh
An efficient one-pot synthesis of chromen-4-ones and isoflavones is achieved directly from phenols via the regio- and chemoselective domino Friedel-Crafts acylation/Allan-Robinson reaction.
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The influence of the aromatic aglycon of galactoclusters on the binding of LecA: a case study with O-phenyl, S-phenyl, O-benzyl, S-benzyl, O-biphenyl and O-naphthyl aglycons

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9166-9179
DOI: 10.1039/C4OB01599A, PaperFrancesca Casoni, Lucie Dupin, Gerard Vergoten, Albert Meyer, Caroline Ligeour, Thomas Gehin, Olivier Vidal, Eliane Souteyrand, Jean-Jacques Vasseur, Yann Chevolot, Francois Morvan
Mannose-centered galactoclusters exhibiting naphthyl or biphenyl aglycons displayed high affinity for LecA.
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Rhodium(II) catalyzed synthesis of macrocycles incorporating oxindole via O-H/N-H insertion reactions

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9243-9256
DOI: 10.1039/C4OB01671H, PaperSengodagounder Muthusamy, Thangaraju Karikalan
Synthesis of 10- to 29-membered oxaza-macrocycles via intramolecular O-H/N-H insertion reactions catalyzed by a rhodium(II) acetate dimer is demonstrated. Synthesis of symmetric macrocycles via head to tail dimerization reactions is also delineated.
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Discovery and synthesis of a novel series of potent, selective inhibitors of the PI3K[small alpha]: 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9157-9165
DOI: 10.1039/C4OB01589D, PaperYong Yin, Xun Wu, Hong-Wei Han, Shao Sha, She-Feng Wang, Fang Qiao, Ai-Min Lu, Peng-Cheng Lv, Hai-Liang Zhu
A series of novel 2-alkyl-chromeno[4,3-c]pyrazol-4(2H)-one derivatives were synthesized and evaluated for their biological activities. Compound 4l exhibited the most potent and selective activity for PI3K[small alpha].
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Synthesis, gelation and topochemical polymerization of meta-linked oligophenylenebutadiynylene derivatives

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9236-9242
DOI: 10.1039/C4OB01322K, PaperIsabelle Levesque, Simon Rondeau-Gagne, Jules Romeo Neabo, Jean-Francois Morin
Rational design of meta-linked oligophenylbutadiynylene (OPBD) derivatives was conducted in order to gain insight into their gelation properties and reactivity toward topochemical polymerization to yield polydiacetylenes (PDAs).
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A theoretical study of ternary indole-cation-anion complexes

5 November, 2014 - 12:17

Org. Biomol. Chem., 2014, 12,9145-9156
DOI: 10.1039/C4OB01879F, PaperJorge A. Carrazana-Garcia, Enrique M. Cabaleiro-Lago, Alba Campo-Cacharron, Jesus Rodriguez-Otero
The simultaneous interactions of an anion and a cation with a [small pi] system were investigated by MP2 and M06-2X theoretical calculations.
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