- Stereospecific 1,4-Metallate Shift Enables Stereoconvergent Synthesis of Ketoximes
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Reported herein is a stereospecific 1,4-metallate rearrangement for single-geometry ketoxime synthesis from oxime chlorides and arylboronic acids. This strategy exhibits broad substrate scope with excellent stereoselectivity under mild reaction conditions. In comparison with the conventional approaches, each configuration of unsymmetric diaryl oximes, as well as the thermodynamically less stable Z isomer of aryl alkyl ketoximes can be selectively and exclusively obtained. The reactivities of unsymmetric diaryl oximes and the Z isomer of aryl alkyl oximes, a class of underexplored molecules, enables efficient access to the corresponding isoquinolines, isoquinoline N-oxides, and amides having a single configuration.
- Yang, Kai,Zhang, Feng,Fang, Tongchang,Zhang, Guan,Song, Qiuling
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p. 13421 - 13426
(2019/08/20)
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- In Situ Generation of Nitrile Oxides from NaCl-Oxone Oxidation of Various Aldoximes and Their 1,3-Dipolar Cycloaddition
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Reported is a new green protocol for the efficient in situ generation of nitrile oxides through NaCl/Oxone oxidation of aldoximes and their dipolar cycloaddition. The key feature is the use of a green chemistry approach to address the substrate scope of aldoximes: broad scope (aliphatic, aromatic, and alkenyl aldoximes) without production of organic byproducts derived from oxidant and/or catalyst. Importantly, NaCl/Oxone-promoted three-component cycloaddition of aldehyde, hydroxylamine hydrochloride, and alkene was demonstrated to be competent (63-81%).
- Zhao, Guodong,Liang, Lixin,Wen, Chi Ho Ethan,Tong, Rongbiao
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supporting information
p. 315 - 319
(2019/01/08)
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- Highly regioselective nitrile oxide dipolar cycloadditions with ortho-nitrophenyl alkynes
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The dipolar cycloadditions of ortho-nitrophenyl alkynes with aryl nitrile oxides has been demonstrated. A range of substituents are tolerated on the alkyne. These reactions proceed with excellent levels of regioselectivity. Subsequent functionalization of the isoxazole scaffold has been demonstrated.
- McIntosh, Melissa L.,Naffziger, Michael R.,Ashburn, Bradley O.,Carter, Rich G.,Zakharov, Lev N.
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p. 9204 - 9213,10
(2012/12/12)
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- A comparative study of the effect of water and organic solvents on 1,3-dipolar cycloaddition reactions of mesitonitrile oxide with c-sulfonyl- and sulfanyl-dithioformates
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1,3-Dipolar cycloadditions of the C-sulfonylated- and sulfanylated- dithioformates with mesitonitrile oxide occurred smoothly in organic and aqueous media to afford 1,4,2-oxathiazoles in good yields. The structures of these cycloadducts have been establis
- El-Sayed, Ibrahim,Ali, Omar M.,Hawata, Mohamed A.,Hegazey, Sally Abou
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scheme or table
p. 1979 - 1985
(2010/11/18)
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- Regioselective synthesis and side-chain metallation and elaboration of 3-aryl-5-alkylisoxazoles
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A number of 3-aryl-5-alkylisoxazoles have been synthesized in high yields by reacting arylnitrile oxides with free enolate ions regioselectively obtained by metallation of various alkyl methyl ketones with LDA in THF at -78°C followed by dehydration. Inve
- Di Nunno, Leonardo,Scilimati, Antonio,Vitale, Paola
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p. 2659 - 2665
(2007/10/03)
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- A facile one-pot preparation of isothiocyanates from aldoximes
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Isothiocyanates 2a-l were prepared in excellent yields in a one-pot reaction from aldoxime derivatives 1a-l by successive treatment of aldoxime with N-chlorosuccinimide (NCS), thiourea, and triethylamine. The use of HCl/DMF/Oxone system in the reaction instead of NCS was equally effective.
- Kim, Jae Nyoung,Jung, Keum Shin,Lee, Hong Jung,Son, Ji Suk
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p. 1597 - 1598
(2007/10/03)
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- (Z)-Stereospecific addition of glycosylmercaptans on nitrilium betaines. Synthesis of 1-S-glucopyranosyl arylthiohydroximates
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With a view to selecting new internal standards for HPLC analysis of glucosinolates, the synthesis of artificial desulfoglucosinolates 5 was carried out.
- Brochard,Joseph,Viaud,Rollin
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p. 1403 - 1414
(2007/10/02)
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