87305-64-4Relevant academic research and scientific papers
A one-pot oxidation/allylation/oxidation sequence for the preparation of β,γ-unsaturated ketones directly from primary alcohols
Moody, Catherine L.,Pugh, David S.,Taylor, Richard J.K.
, p. 2511 - 2514 (2011)
A one-pot oxidation/allylation/oxidation procedure has been developed for the conversion of primary alcohols into β,γ-unsaturated ketones. The methodology has been applied to a range of alcohols, and in some cases, isomerisation to produce the corresponding α,β-unsaturated ketones has been carried out.
Organocatalytic Asymmetric Synthesis of Cyclic Acetals with Spirooxindole Skeleton
Shikari, Amit,Mandal, Koushik,Chopra, Deepak,Pan, Subhas Chandra
, p. 58 - 63 (2021/11/09)
An organocatalytic asymmetric synthesis of cyclic acetal with spirooxindole skeleton has been developed via a domino reaction between isatin and γ-hydroxy enones. Bifunctional squaramide catalyst with adamantyl motif was found to be the most effective for the cascade reaction. With 10 mol% of the catalyst, the desired products were obtained in 1.8:1 to 9:1 diastereo- and 86% to >99% enantioselectivities from a range of substituted isatins and γ-hydroxy enones. (Figure presented.).
Copper-catalyzed radical oxyallylation of olefins for the construction of alkene-containing isoxazolines
He, Xiaoxue,Qian, Lijie,Dai, Yuyu,Yan, Xinhuan,Li, Xiaoqing,Xu, Xiangsheng
, (2021/05/31)
A radical-mediated approach to alkene oxyallylation using allylic oximes is described. The reaction proceeds under copper-catalytic redox-neutral conditions and tolerates various functional groups. This protocol thus enables the synthesis of structurally valuable isoxazolines and the introduction of a versatile olefin motif in a single step.
Ruthenium-Catalyzed Direct Transformation of Alkenyl Oximes to 5-Cyanated Isoxazolines: A Cascade Approach Based on Non-Stabilized Radical Intermediate
Wang, Dan-Jun,Chen, Bei-Yi,Wang, Yi-Qi,Zhang, Xiao-Wei
, p. 1342 - 1346 (2018/04/02)
A ruthenium-catalyzed ammoxidation of alkenyl oximes under mild and neutural condtions is described. In this method, tert-butyl nitrite plays a dual role, acting as an oxidant as well as a nitrogen source. This reaction avoids using any toxic radical initiators or cyanide reagents. This convenient and practical method offers an easy access to 5-cyanated isoxazolines in good to high yields, and shows good functional group tolerance and high efficiency. It is rather remarkable that this new reaction provides a strategically distinct approach based on non-stabilized radical intermediate and constructs C–O and C≡N triple bonds in a single-step. Moreover, the difunctionalization of unactivated olefins bearing oximes has been realized.
Copper-mediated oxysulfonylation of alkenyl oximes with sodium sulfinates: a facile synthesis of isoxazolines featuring a sulfone substituent
Wang, Li-Jing,Chen, Manman,Qi, Lin,Xu, Zhidong,Li, Wei
, p. 2056 - 2059 (2017/02/15)
A novel and efficient Cu(OAc)2-mediated oxysulfonylation of alkenyl oximes with sodium sulfonates was developed. The reactions are easy to conduct, occur under mild conditions, and form a broad range of sulfone-substituted isoxazolines in good yields.
Green organocatalytic synthesis of isoxazolines via a one-pot oxidation of allyloximes
Triandafillidi, Ierasia,Kokotos, Christoforos G.
, p. 106 - 109 (2017/11/27)
A green, sustainable, organocatalytic, and efficient synthesis of isoxazolines from allyloximes was developed. A 2,2,2-trifluoroacetophenone-catalyzed oxidation of allyloximes, utilizing H2O2 as the green oxidant, was taken advantage of in order to introduce a cheap and environmentally friendly protocol for the synthesis of substituted isoxazolines. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated, leading to isoxazolines in moderate to excellent yields.
Metal-Free Autoxidative Nitrooxylation of Alkenyl Oximes with Molecular Oxygen
Zhang, Xiao-Wei,Xiao, Zu-Feng,Zhuang, Yan-Jun,Wang, Mei-Mei,Kang, Yan-Biao
, p. 1942 - 1945 (2016/07/06)
A metal-free aerobic autoxidative nitrooxylation of alkenyl oximes mediated by tert-butyl nitrite is described. Molecular oxygen is used as the oxidizing reagent, avoiding use of organic trapping reagents such as 2,2,6,6-tetramethylpiperidine 1-oxyl (TEMP
Transition-metal-free oxychlorination of alkenyl oximes:: In situ generated radicals with tert -butyl nitrite
Zhang, Xiao-Wei,Xiao, Zu-Feng,Wang, Mei-Mei,Zhuang, Yan-Jun,Kang, Yan-Biao
, p. 7275 - 7281 (2016/08/05)
Oxychlorination of alkenyl oximes is harder compared to the analogous oxybromination or oxyiodination because of the difficulty associated with the formation of chlorine cations or radicals. A transition-metal-free oxychlorination of alkenyl oximes has be
Iodine(III)-Mediated Oxy-fluorination of Alkenyl Oximes: An Easy Path to Monofluoromethyl-Substituted Isoxazolines
Kong, Weidong,Guo, Quanping,Xu, Zhaoqing,Wang, Guoqiang,Jiang, Xianxing,Wang, Rui
, p. 3686 - 3689 (2015/08/18)
A highly regioselective intramolecular oxy-fluorination of alkenyl oximes was achieved. This new transformation represents an efficient method for the preparation of monofluoromethyl-substituted isoxazolines. The synthetic application of the oxy-fluorinat
Copper-catalyzed oxyazidation of unactivated alkenes: A facile synthesis of isoxazolines featuring an azido substituent
Zhu, Liping,Yu, Hongmei,Xu, Zhaoqing,Jiang, Xianxing,Lin, Li,Wang, Rui
, p. 1562 - 1565 (2014/04/17)
A novel and efficient Cu(OAc)2-catalyzed oxyazidation of unactivated alkenes was developed. The reactions are easy to conduct, occur under mild conditions, and form azido-substituted isoxazolines in good yields.
