- Synthesis of a protected derivative of (±)-1-(hydroxymethyl)conduritol C from 2-(hydroxymethyl)furan
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A short and totally stereoselective synthesis of a protected derivative of (±)-1-(hydroxymethyl)conduritol C has been achieved. The key step was the cleavage of the oxygen bridge in a 7-oxanorbomenic sulfone using an acidic medium.
- Arjona, Odon,Iradier, Fatima,Manas, Rosario M.,Plumet, Joaquin
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- The diels-alder cycloaddition reaction of some substituted furans and E- 1,2-bis(phenylsulfonyl)ethylene
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The Diels-Alder cycloaddition between several 2-, and 3-substituted furans and E-1,2-bis(phenylsulfonyl)ethylene have been carried out in high yields. Stereoselectivity observed in the case of 2-sustituted furans has been explained by means of the MM3-tra
- Arjona, Odon,Iradier, Fatima,Manas, Rosario M.,Plumet, Joaquin,Grabuleda, Xavier,Jaime, Carlos
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- Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
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A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
- Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
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p. 4159 - 4170
(2021/03/09)
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- Force-mediated molecule release from double network hydrogels
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The incorporation of mechanosensitive linkages into polymers has led to materials with dynamic force responsivity. Here we report oxanorbornadiene cross-linked double network hydrogels that release molecules through a force-mediated retro Diels-Alder reaction. The molecular design and tough double network of polyacrylamide and alginate promote significantly higher activation at substantially less force than pure polymer systems. Activation at physiologically relevant forces provides scope for instilling dynamic mechanochemical behavior in soft biological materials. This journal is
- Buche, Michael Robert,Huang, Yuwan,Islam, Md Shariful,Jayathilaka, Pavithra Bhakthi,Kilian, Kristopher Alan,Kruzic, Jamie Joseph,Molley, Thomas Gregory,Silberstein, Meredith Natania
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supporting information
p. 8484 - 8487
(2021/09/08)
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- Open-Close Strategy toward the Organocatalytic Generation of 2-Deoxyribosyl Oxocarbenium Ions: Pyrrolidine-Salt-Catalyzed Synthesis of 2-Deoxyribofuranosides
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The reaction of secondary amine salts with 2-deoxy-ribofuranoses under forcible conditions leads to the putative furanosyl oxocarbenium ion that is trapped with various alcohols to provide 2-deoxy-ribofuranosides. The observed anomeric selectivities range from an equimolar mixture to complete α-selectivity in the case of bulky sugar acceptors. Owing to the mechanism and temperature of the transformation, the generated oxocarbenium ion shows little or no facial preference towards the nucleophilic attack of non-carbohydrate acceptors and leads to a mixture of anomers in the case of benzyl and acetyl protected donors. However, the conformationally less flexible tetraisopropylsilyl protected donor reacted with both sugar and non-sugar acceptors in a stereoselective fashion. Besides, the glycosylation with 2-cyanoethanol gave the product with unexpected beta-selectivity presumably due to nitrile effect. The operationally simple organocatalytic protocol provides easy access to otherwise difficult 2-deoxy-ribofuranosides/disaccharides.
- Ghosh, Titli,Mukherji, Ananya,Kancharla, Pavan K.
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p. 7488 - 7498
(2019/11/29)
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- Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation
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A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path.
- Bao, Yan,Wang, Jian-Yong,Zhang, Ya-Xuan,Li, Yan,Wang, Xi-Sheng
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supporting information
p. 3147 - 3150
(2018/07/13)
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- JAK2 JH2 Fluorescence Polarization Assay and Crystal Structures for Complexes with Three Small Molecules
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A competitive fluorescence polarization (FP) assay is reported for determining binding affinities of probe molecules with the pseudokinase JAK2 JH2 allosteric site. The syntheses of the fluorescent 5 and 6 used in the assay are reported as well as Kd results for 10 compounds, including JNJ7706621, NVP-BSK805, and filgotinib (GLPG0634). X-ray crystal structures of JAK2 JH2 in complex with NVP-BSK805, filgotinib, and diaminopyrimidine 8 elucidate the binding poses.
- Newton, Ana S.,Deiana, Luca,Puleo, David E.,Cisneros, José A.,Cutrona, Kara J.,Schlessinger, Joseph,Jorgensen, William L.
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supporting information
p. 614 - 617
(2017/06/13)
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- Palladium-catalyzed C-H homocoupling of furans and thiophenes using oxygen as the oxidant
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A general and efficient palladium-catalyzed intermolecular direct C-H homocoupling of furans and thiophenes has been developed. The reaction is characterized by using molecular oxygen as the sole oxidant and complete C5-position regioselectivity. Both C2- and C3-substituted furans or thiophenes are appropriate substrates. The approach provides a straightforward, facile, and economical route to bifurans and bithiophenes under mild reaction conditions.
- Li, Na-Na,Zhang, Yan-Lei,Mao, Shuai,Gao, Ya-Ru,Guo, Dong-Dong,Wang, Yong-Qiang
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supporting information
p. 2732 - 2735
(2014/06/09)
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- Selective rhodium(III)-catalyzed cross-dehydrogenative coupling of furan and thiophene derivatives
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A hot couple: An unprecedented rhodium(III)-catalyzed cross-dehydrogenative coupling (CDC) of various furan and thiophene derivatives leads to valuable 2,2'-bi(heteroaryl) products in good yields and selectivities (see scheme). In addition, pyrroles and indoles can also be used as coupling partners, giving C3-arylated products. Copyright
- Kuhl, Nadine,Hopkinson, Matthew N.,Glorius, Frank
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supporting information; experimental part
p. 8230 - 8234
(2012/09/08)
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- Synthesis of allenyl ketones and their palladium-catalyzed cycloisomerization/dimerization: Approaching the limits
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The preparation of several new allenyl ketones 1a-j and 1o-q is reported. In the case of allenyl ketones with nucleophilic groups in the side-chain like 1k-m, the material polymerized during the purification procedure; with the dialkyl thioether In the product of a Pummerer isomerization, the acetoxymethyl alkyl thioether, 11 was formed. Depending on the route to 1 sometimes either the acetate adducts 8 and the 1-propynyl ketones 9 or the dipropargyl and propargyl allenyl carbinol 14 and 15 were observed as side-products. Good yields of the sensitive aryl γ-halogen-allenyl ketones 23a and 23b were obtained by a new synthetic route, on the other hand the aryl γ-silylallenyl ketone 23c was readily desilylated. Subjecting the new allenyl ketones to the PdCl2(MeCN)2 catalyst provided the 2-substituted furans 2 and the 2,4-disubstituted furans 3 in most cases. The yields and ratios of these products strongly depended on the nature of the groups being present. With the aryl thioether and the γ-halogen allenyl ketones the palladium-catalyzed reaction failed. Detailed structural information about the new products was provided by the X-ray structure analyses of the p-acetamidophenyl propargyl carbinol 6g and the 2-aryl-4-(1-methyl-3-aryl-3-oxo-propen-1-yl furan 3h. Wiley-VCH Verlag GmbH, 1999.
- Hashmi, A. Stephen K.,Choi, Ji-Hyun,Bats, Jan W.
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p. 342 - 357
(2007/10/03)
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- Synthesis of cyclopentenones 2- and 2,4-oxygenated from furfural
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2-Benzyloxy-4-methoxy-2-cyclopentenone and 2-benzyloxy-2-cyclopentenone were efficiently prepared using furfuryl alcohol as the starting material. The synthetic route employed in both cases involves the previous preparation of a ketoaldehyde that is subsequently cyclized to the parent cyclopentenone. Each stage of this route involves reactions of very low cost, with simple synthetic procedures and very good yields.
- E Silva, Natalia R. Da. F.,De Magalhaes, Gouvan C.
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p. 1477 - 1483
(2007/10/03)
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- Synthesis of alkyl heteryl ethers from acetates under interphase catalysis conditions in a liquid/solid system
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The reaction of acetates of heterocyclic alcohols with alkyl halides in the two-phase catalytic system of solid KOH/C6H6/18-crown-6 at room temperature leads selectively to the formation of the corresponding heterocyclic ethers in 32-93% yield. 1998 Plenum Publishing Corporation.
- Abele,Abele,Gaukhman,Lukevics
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- Influence of Arene Substituents on the Mode and Regiochemistry of Photocycloaddition of Furan to the Benzene Ring
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Furan undergoes (2+2), (2+3), (4+3) and (4+4) photocycloadditions to the benzene ring.The reaction mode selectivity and regiochemistry of the addition are markedly dependent on the arene substituents, but unlike the photoaddition of ethenes to the benzene
- Garcia, Hermengildo,Gilbert, Andrew,Griffiths, Owain
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p. 247 - 252
(2007/10/02)
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- STEREOSPECIFIC SYNTHESIS OF METHYL D,L-HEX-2-ULOPYRANOSIDES FROM FURAN COMPOUNDS
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2-Benzyloxymethyl-5-hydroxymethylfuran was converted, according to the known method, into methyl 1-O-benzyl-3,4-dideoxy-D,L-hex-3-en-2-ulopyranos-5-ulose.Reduction of the latter and hydroxylation or epoxidation, followed by the oxirane ring opening, afforded the title compounds with α-sorbo-, β-fructo-, α-tagato- and α-psico- configuration.The steric course of reduction, hydroxylation and epoxidation reactions were examined.
- Achmatowicz, Osman,Burzynska, Maria H.
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p. 3507 - 3513
(2007/10/02)
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