- An efficient synthesis of 2-isoxazolines from α-haloketone oximes and dimethyl sulfonium salts
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2-Isoxazolines were synthesized efficiently from a formal [4+1] cycloaddition of nitrosoalkenes and sulfur ylides, which were generated in situ from α-haloketone oximes and dimethyl sulfonium salts. This approach provides a new method to synthesize a rang
- Zhao, Sen,Wang, Hang,Sun, Shaofa,Guo, Haibing,Chen, Zhiyu,Wang, Jian,Wang, Lu,Liang, Steven,Wang, Gangqiang
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supporting information
p. 382 - 385
(2019/01/04)
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- Visible-light-mediated generation of nitrile oxides for the photoredox synthesis of isoxazolines and isoxazoles
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Visible-light photoredox catalysis enables the synthesis of biologically relevant isoxazolines and isoxazoles from hydroxyimino acids. The process shows broad functional group compatibility and mechanistic and computational studies support a visible-light-mediated generation of nitrile oxides by two sequential oxidative single electron transfer processes.
- Svejstrup, Thomas D.,Zawodny, Wojciech,Douglas, James J.,Bidgeli, Damon,Sheikh, Nadeem S.,Leonori, Daniele
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p. 12302 - 12305
(2016/10/22)
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- 3-Aryl-5-vinyl-2-isoxazolines and 3-aryl-5-vinylisoxazoles from aryl nitrile oxides and methyl vinyl ketone lithium enolate: Reaction limits and synthetic utility exploitation
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3-Aryl-5-hydroxy-5-vinyl-2-isoxazolines were synthesized by reacting aryl nitrile oxides with the lithium enolate of methyl vinyl ketone (MVK) at-78 °C. Fair to good yields are obtained in the case of aryl nitrile oxides bearing electron-withdrawing group
- Salomone, Antonio,Scilimati, Antonio,Vitale, Paola
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p. 807 - 816
(2015/03/14)
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- 3-aryl-5-vinyl-2-isoxazolines and 3-aryl-5-vinylisoxazoles from aryl nitrile oxides and methyl vinyl ketone lithium enolate: Reaction limits and synthetic utility exploitation
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3-Aryl-5-hydroxy-5-vinyl-2-isoxazolines were synthesized by reacting aryl nitrile oxides with the lithium enolate of methyl vinyl ketone (MVK) at -78 °C. Fair to good yields are obtained in the case of aryl nitrile oxides bearing electron-withdrawing grou
- Salomone, Antonio,Scilimati, Antonio,Vitale, Paola
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- 2-Isoxazolines with an electron-acceptor substituent at C(5) in reactions with nucleophilic reagents
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Depending on the substituent at position 5 of the heterocycle, reaction of 2-isoxazolines with K-selectride, molybdenum hexacarbonyl, dimsyl sodium, and butyl lithium gave 1,3-cyclo-decomposition, aromatization of the isoxazoline ring, or reduction of the functional groups in the substituted isoxazolines.
- Koroleva,Bondar,Katok,Chekanov,Chernikhova
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p. 362 - 369
(2008/09/21)
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- 5-Hydroxy-3-phenyl-5-vinyl-2-isoxazoline and 3-phenyl-5-vinylisoxazole: Synthesis and reactivity
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5-Hydroxy-3-phenyl-5-vinyl-2-isoxazoline has been synthesized by reacting benzonitrile oxide with the enolate ion of methyl vinyl ketone. From 5-hydroxy-5-vinyl-2-isoxazoline, 5-vinylisoxazole was then quantitatively obtained by dehydration-aromatization
- Di Nunno, Leonardo,Scilimati, Antonio,Vitale, Paola
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p. 11270 - 11278
(2007/10/03)
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- 1,3-Dipolar cycloadditions of benzonitrile oxide with various dipolarophiles in aqueous solutions. A kinetic study
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The second-order rate constants for the 1,3-dipolar cycloaddition of benzonitrile oxide (1) with various dipolarophiles (2a-e) were determined in aqueous media and in organic solvents to gain more insight into the influence of an aqueous medium on pericyclic reactions. 1,3-Dipolar cycloadditions with electron-poor dipolarophiles are accelerated in water and protic solvents, whereas an aqueous medium has no special effect when electron-poor dipolarophiles are involved. These observations can be explained using frontier molecular orbital theory. In all cases, enforced hydrophobic interactions promote the reaction. These results are supported by kinetic experiments in waterethanol mixtures. Sodium dodecyl sulfate micelles accelerate the cycloaddition of 1 with both electron-rich and electron-poor dipolarophiles. More than for other systems, the present results show that hydrogen bonding and hydrophobic interactions can either cooperate or counteract each other in determining the kinetic medium effects in aqueous solutions.
- Van Mersbergen, Dick,Wijnen, Jan W.,Engberts, Jan B. F. N.
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p. 8801 - 8805
(2007/10/03)
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- A Highly Effective Quenching Method of 1,3-Dipolar Cycloadditions of Nitrile Oxides or Nitrile Oxide/Lewis Acid Complexes by Use of 2-Propenyloxymagnesium Bromide
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2-Propenyloxymagnesium bromide, readily prepared by treating 2-propen-1-ol with EtMgBr, is a highly effective quencher of nitrile oxide cycloadditions since this alkoxide is much more reactive to nitrile oxides than any other ever known dipolarophiles of
- Kanemasa, Shuji,Nishiuchi, Masaki
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p. 4011 - 4014
(2007/10/02)
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- Nucleophilic Additions to and Reductions of 5-Formyl- and 5-Acyl-2-isoxazolines (4,5-Dihydroisoxazoles): A Stereoselective Route to β,γ-Dihydroxy Ketones
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Reductions of readily available 5-acyl-2-isoxazolines with L-Selectride follow the Felkin-Anh model and produce syn-5-hydroxyalkyl-2-isoxazolines with excellent (>95:5) selectivities.Swern oxidation of 5-hydroxymethyl-2-isoxazolines, followed by direct ad
- Curran, Dennis P.,Zhang, Jiancun
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p. 2613 - 2625
(2007/10/02)
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- Some Acylations of 3-Phenyl and 3-Mesityl-4,5-dihydroisoxazoles
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A study on the acetylation and benzoylation of title compounds by quenching the corresponding 4-carbanions with acyl chlorides or esters is reported.The obtained ketones are formed as minor regioisomeric adducts in the cycloadditions of benzo and mesitoni
- Corsaro, Antonino,Chiacchio, Ugo,Perrini, Giancarlo,Caramella, Pierluigi,Albini, Franca Marinone
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p. 1691 - 1699
(2007/10/02)
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- REACTIONS OF 2-ALKOXY-1,3-DIENES WITH NITRILE OXIDES AND ARYL AZIDES
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The chemoselectivity in the addition of the oxides of benzonitrile and benzoyl cyanide and p-nitrophenyl and p-nitrobenzoyl azides to 2-methoxy-, 2-ethoxy-, 2-isopropoxy-, and 2-tert-butoxy-1,3-butadienes and also to 2-methoxy-3-methyl-1,3-butadiene was i
- Kheruze, Yu. I.,Galishev, V. A.,Petrov, A. A.
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p. 852 - 856
(2007/10/02)
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- BAKER'S YEAST REDUCTION OF 5-ACETYL-2-ISOXAZOLINES SYNTHESIS OF ENANTIOMERICALLY PURE 2,3-DIHYDROXY KETONES AND 1,2,4-TRIOLS
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Saccharomyces cerevisiae reduces enantioselectively racemic 5-acetyl-2-isoxazolines to 5-ethanol-2-isoxazolines in high yields and high enantiomeric excess.Subsequent ring hydrogenolysis of the alcohols thus produced leads to enantiomerically pure 2,3-dih
- Ticozzi, Calimero,Zanarotti, Antonio
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p. 6167 - 6170
(2007/10/02)
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- Utilization of Vinylsilanes in Cycloaddition Reactions
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The reaction of several vinylsilanes with benzonitrile oxide, 2-diazopropane, C-carboethoxy-N-phenylnitrile imine, and substituted 1,3-butadienes has been examined.The 1,3-dipolar cycloadditions followed frontier orbital predictions and gave silylated iso
- Padwa, Albert,MacDonald, J. Gavin
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p. 3189 - 3195
(2007/10/02)
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- SILYL NITRONATES IN ORGANIC SYNTHESIS. SYNTHESIS OF 3(2H)-FURANONES
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A synthesis of 3(2H)-furanones, a structural element of several natural products, has been developed in which silyl nitronates or nitrile oxides are condensed with vinyl ketones to form 5-acyl-2-isoxazolines which are reduced with titanous ions or catalytically to 1,4-diketo-2-ols and cyclized with sodium acetate in acetic acid.
- Andersen, Soeren H.,Sharma, K. K.,Torssell, Kurt, B. G.
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p. 2241 - 2246
(2007/10/02)
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- 1,3-DIPOLAR CYCLOADDITION OF BENZONITRILE OXIDE WITH VINYLSILANES
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The reaction of benzonitrile oxide with several vinylsilanes has been found to afford silylated isoxazoles.Relative rates for the cycloaddition reaction were determined.
- Padwa, Albert,MacDonald, J. Gavin
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p. 3219 - 3222
(2007/10/02)
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