Org. and Biomol. Chem.
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The anomeric effect on the basis of natural bond orbital analysis
DOI: 10.1039/C3OB40187A, PaperMatheus P. Freitas
The anomeric effect in some 2-substituted tetrahydropyrans has been investigated using natural bond orbital (NBO) analysis and its origin was found to be dependent on the substituent and the medium.
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Racemization of enantiopure secondary alcohols by Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase
DOI: 10.1039/C3OB27415B, PaperMusa M. Musa, Robert S. Phillips, Maris Laivenieks, Claire Vieille, Masateru Takahashi, Samir M. Hamdan
Alcohol dehydrogenase-catalyzed racemization of enantiopure secondary alcohols is described.
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Sequential enantiodivergent organocatalysis: reversibility in enantioswitching controlled by a conformationally flexible guanidine/bisthiourea organocatalyst
DOI: 10.1039/C3OB27479A, PaperYoshihiro Sohtome, Takahisa Yamaguchi, Shinji Tanaka, Kazuo Nagasawa
Here we describe our studies on solvent-dependent enantiodivergent Mannich-type reactions utilizing conformationally flexible guanidine/bisthiourea organocatalyst (S,S)-1.
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Concise total syntheses of (+/-)-noruleine and (+/-)-uleine
DOI: 10.1039/C3OB40180D, PaperSuleyman Patir, Erkan Erturk
The first total synthesis of (+/-)-noruleine and a concise synthesis of (+/-)-uleine have been accomplished.
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Direct acylation of N-benzyltriflamides from the alcohol oxidation level via palladium-catalyzed C-H bond activation
DOI: 10.1039/C3OB40140E, PaperJihye Park, Aejin Kim, Satyasheel Sharma, Minyoung Kim, Eonjeong Park, Yukyoung Jeon, Youngil Lee, Jong Hwan Kwak, Young Hoon Jung, In Su Kim
A palladium-catalyzed ortho-acylation of N-benzyltriflamides from the alcohol oxidation level via C-H bond activation is described.
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Enzyme-mediated nutrient release: glucose-precursor activation by [small beta]-galactosidase to induce bacterial growth
DOI: 10.1039/C3OB27385G, PaperNaama Karton-Lifshin, Uwe Vogel, Eran Sella, Peter H. Seeberger, Doron Shabat, Bernd Lepenies
A masked glucose precursor that is activated by [small beta]-galactosidase was used as a carbon source for bacterial growth in a glucose-deficient medium.
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A silver(I)-catalyzed tandem reaction of 2-alkynylbenzaldoximes with ketenes
DOI: 10.1039/C3OB27427F, PaperHongliang Liu, Gang Liu, Shouzhi Pu, Zhiyong Wang
A silver triflate-catalyzed tandem reaction of 2-alkynylbenzaldoximes with ketenes proceeds through 6-endo-cyclization, [3 + 2] cycloaddition and rearrangement, leading to isoquinoline derivatives in moderate to good yields.
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Low-molecular-weight gelators consisting of hybrid cyclobutane-based peptides
DOI: 10.1039/C3OB27347D, PaperSergi Celis, Pau Nolis, Ona Illa, Vicenc Branchadell, Rosa M. Ortuno
Nice gels have been formed whose morphology, structure and gelation dynamics were investigated using experimental techniques and computational calculations.
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The syn and anti isomers of the porphyrinogen-like precursor of calix[4]phyrin: isolation, X-ray structure, anion binding and fluoride-ion-mediated proton-deuterium exchange studies
DOI: 10.1039/C3OB40147B, PaperTapas Guchhait, Vikesh Kumar Jha, Ganesan Mani
The X-ray structures of the syn and anti isomers of the porphyrinogen-like precursor of a calix[4]phyrin molecule, their anion binding and the characteristic solution state structures of their F- ion complexes as identified by 19F NMR are reported.
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Electrophilic monoiodination of terminal alkenes
DOI: 10.1039/C3OB27348B, PaperSergiy V. Yemets, Tatyana E. Shubina, Pavel A. Krasutsky
An excess of elemental iodine in DMA enables effective 3/iodanylium-de-hydronation of terminal alkenes with 3-iodopropene derivatives and HI formation within minutes at room temperature. The molar ratio of iodine to substrate was decreased to 1 : 1 when HI formed was oxidized on a platinum anode. The reaction mechanism is studied.
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Copper-catalyzed aromatic C-H bond halogenation with lithium halides under aerobic conditions
DOI: 10.1039/C3OB40185E, CommunicationSong Mo, Yamin Zhu, Zengming Shen
A concise and practical Cu-catalyzed protocol for the preparation of chloro- and bromoarenes via C-H bond activation has been developed.
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N-terminal dual protein functionalization by strain-promoted alkyne-nitrone cycloaddition
DOI: 10.1039/C3OB00043E, PaperRinske P. Temming, Loek Eggermont, Mark B. van Eldijk, Jan C. M. van Hest, Floris L. van Delft
Strain-promoted alkyne-nitrone cycloaddition (SPANC) is employed to simultaneously introduce two functional groups into the cell-penetrating peptide hLF or the enhanced green fluorescent protein, in a one-pot reaction.
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Photochemical reactions of tetrachloro-1,4-benzoquinone (chloranil) with tricyclo[4.1.0.02,7]heptane (Moore's hydrocarbon) and bicyclo[4.1.0]hept-2-ene (2-norcarene)
DOI: 10.1039/C3OB27305A, PaperManfred Christl, Max Braun, Oliver Deeg
The irradiation of chloranil in the presence of Moore's hydrocarbon gave two bis(endo-2-norcaryl) ethers of 2,3,5,6-tetrachlorohydroquinone and three cycloadducts of 2-norcarene.
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A stereoselective synthesis of the C9-C19 subunit of (+)-peloruside A
DOI: 10.1039/C3OB27508F, PaperSadagopan Raghavan, V. Vinoth Kumar
A stereoselective synthesis of the C9-C19 subunit of peloruside A is disclosed utilizing metal catalyzed catalytic asymmetric transformations, substrate controlled induction and enzymatic resolution.
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New trends in bismuth-catalyzed synthetic transformations
DOI: 10.1039/C3OB26537D, Emerging AreaThierry Ollevier
This review highlights the most recent uses of bismuth catalysis with a special emphasis on emerging applications and challenging synthetic transformations.
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First Total Synthesis of Nhatrangin A
Org. Biomol. Chem., 2013, Accepted Manuscript
DOI: 10.1039/C3OB40252E, PaperAhmed Kamal, Saidi Reddy Vangala
The first total synthesis of nhatrangin A has been achieved. Pivotal bond forming events in the synthesis include Brown crotylboration, olefin cross metathesis, Sharpless asymmetric dihydroxylation and Yamaguchi esterification.
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DOI: 10.1039/C3OB40252E, PaperAhmed Kamal, Saidi Reddy Vangala
The first total synthesis of nhatrangin A has been achieved. Pivotal bond forming events in the synthesis include Brown crotylboration, olefin cross metathesis, Sharpless asymmetric dihydroxylation and Yamaguchi esterification.
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Facile dimethylarsenic exchange and pyramidal inversion in its cysteine and glutathione adducts
DOI: 10.1039/C3OB40268A, CommunicationD. Scott Bohle, Yuxuan Gu
Biologically relevant dimethylarsenic(III) species are shown to have labile As-S bonds, we attempted to measure the kinetics of this interaction using dynamic NMR and proposed mechanisms for this interaction. Implications to arsenic drug therapy and arsenic poisoning.
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Synthetic use of the primary kinetic isotope effect in hydrogen atom transfer 2: generation of captodatively stabilised radicals
DOI: 10.1039/C3OB40275D, PaperMark E. Wood, Sabine Bissiriou, Christopher Lowe, Kim M. Windeatt
Intramolecular hydrogen atom transfer in morpholin-2-ones illustrates the extent to which radical stability can offset the primary kinetic isotope effect.
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Remarkable effect of CF3CH2OH for the halogen induced oxidative rearrangement reaction of aminals leading to 3,4-dihydroquinazolines
DOI: 10.1039/C3OB40132D, PaperKenichi Murai, Masato Shimura, Ryu Nagao, Daisuke Endo, Hiromichi Fujioka
CF3CH2OH was found to be a useful solvent for the oxidative rearrangement reactions of aminals promoted by N-chlorosuccinimide, which proceed via the intermediacy of in situ formed chloro-aminals and that produce 3,4-dihydroquinazolines.
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Aqueous synthesis of N,S-dialkylthiophosphoramidates: design, optimisation and application to library construction and antileishmanial testing
DOI: 10.1039/C3OB27448A, PaperMilena Trmcic, Frances L. Chadbourne, Paul M. Brear, Paul W. Denny, Steven L. Cobb, David R. W. Hodgson
Effective aqueous N-thiophosphorylation of key biomolecules was observed. S-Alkylation was also explored to prepare phosphodiester mimics.
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