89703-88-8Relevant academic research and scientific papers
Conformationally Biased Ketones React Diastereoselectively with Allylmagnesium Halides
Bartolo, Nicole D.,Demkiw, Krystyna M.,Read, Jacquelyne A.,Valentín, Elizabeth M.,Yang, Yingying,Dillon, Alexandra M.,Hu, Chunhua T.,Ward, Michael D.,Woerpel
, p. 3042 - 3065 (2022/02/25)
The addition of the highly reactive reagent allylmagnesium halide to α-substituted acyclic chiral ketones proceeded with high stereoselectivity. The stereoselectivity cannot be analyzed by conventional stereochemical models because these reactions do not conform to the requirements of those models. Instead, the stereoselectivity arises from the approach of the nucleophile to the most accessible diastereofaces of the lowest-energy conformations of the ketones. High stereoselectivity is expected, and the stereochemical outcome can be predicted, with conformationally biased ketones that have sterically distinguishable diastereofaces wherein only one face is accessible for nucleophilic addition. The conformations of the ketones can be determined by a combination of computational modeling and, in some cases, structure determination by X-ray crystallography.
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
supporting information, 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.
Alkyne hydroacylation: Switching regioselectivity by tandem ruthenium catalysis
Chen, Qing-An,Cruz, Faben A.,Dong, Vy M.
, p. 3157 - 3160 (2015/03/30)
By using tandem Ru-catalysis, internal alkynes can be coupled with aldehydes for the synthesis of β,γ-unsaturated ketones. The catalyst promotes alkyne transformations with high regioselectivity, with examples that include the differentiation of a methyl vs ethyl substituent on the alkyne. Mechanistic studies suggest that the regioselectivity results from a selective allene formation that is governed by allylic strain.
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
supporting information, 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.
Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin
Dong, Kui-Yong,Qin, Hai-Tao,Bao, Xing-Xing,Liu, Feng,Zhu, Chen
supporting information, p. 5266 - 5268 (2015/01/09)
A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).
Oxime radical promoted dioxygenation, oxyamination, and diamination of alkenes: Synthesis of isoxazolines and cyclic nitrones
Han, Bing,Yang, Xiu-Long,Fang, Ran,Yu, Wei,Wang, Chao,Duan, Xiao-Yong,Liu, Shuai
supporting information; experimental part, p. 8816 - 8820 (2012/10/18)
Up the tempo: The intramolecular addition of oxime radicals to C=C bonds was achieved by using DEAD and TEMPO to give 4,5-dihydroisoxazoles as a result of a C=O bond-forming, 5-exo-trig cyclization. γ,δ-Unsaturated ketoximes also reacted to afford cyclic nitrones through C-N bond formation. The reactions offer a metal-free approach for the vicinal difunctionalization of unactivated alkenes. Copyright
Organometallic-type reactions in aqueous media mediated by indium. Allylation of acyloyl-imidazoles and pyrazoles. Regioselective synthesis of β,γ-unsaturated ketones.
Bryan, Vernal J.,Chan, Tak-Hang
, p. 6493 - 6496 (2007/10/03)
Indium mediated coupling of allylic bromide with acyloyl-imidazoles or pyrazoles in aqueous media gives the corresponding tertiary alcohols or ketones in good yield. The reaction provides a facile regioselective synthesis of P,β,γ-unsaturated ketones and its usefulness is demonstrated by the synthesis of the monoterpene artemesia ketone.
The Stereochemical Assignment of the 1,2-Diphenylbut-3-en-1-ols, (1RS,2RS,3RS)- and (1RS,2RS,3SR)-3,4-Epoxy-1,2-diphenylbutan-1-ols and (2RS,3SR)- and (2RS,3RS)-3,4-Epoxy-1,2-diphenylbutan-1-ones and Crystal Structure of (1RS,2RS,3RS)-3,4-Epoxy-1,2-diphen
Coxon, James M.,Simpson, Gregory W.,Steel, Peter J.,Trenerry, V. Craige
, p. 65 - 72 (2007/10/02)
The reaction of the Grignard compound formed from (E)-3-chloro-1-phenylprop-1-ene (2a) with benzaldehyde has been studied and conditions found which allow for the efficient preparation of the diastereoisomeric homoallylic alcohols (4) and (5).The relative
