10457-70-2Relevant academic research and scientific papers
Stereospecific Electrophilic Fluorocyclization of α,β-Unsaturated Amides with Selectfluor
Fei, Haiyang,Fu, Yao,Jalani, Hitesh B.,Li, Guigen,Lu, Hongjian,Wu, Hongmiao,Xu, Zheyuan,Zhu, Lin
, (2020/03/30)
An efficient fluorocyclization of α,β-unsaturated amides through a formal halocyclization process is developed. The reaction proceeds under transition-metal-free conditions and leads to the formation of fluorinated oxazolidine-2,4-diones with excellent regio- and diastereoselectivity. The evaluation of the reaction mechanism based on preliminary experiments and density functional theory calculations suggests that a synergetic syn-oxo-fluorination occurs and is followed by an anti-oxo substitution reaction. The reaction opens a new window in the field of stereospecific fluorofunctionalization.
METHOD FOR PREPARING MULTI-SUBSTITUTED ACRYLIC ACID COMPOUND
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Paragraph 0014; 0015; 0038; 0039, (2019/02/13)
A method for preparing a multi-substituted acrylic acid compound includes steps as follow. A reaction solution is provided, wherein the reaction solution includes an organometallic reagent, a nickel-containing metal catalyst, a catalyst ligand, a first solvent, and the organometallic reagent is a Grignard reagent or a Gilman reagent. An addition step is conducted, wherein an alkyne compound is mixed with the reaction solution so as to undergo an addition reaction, thus an intermediate solution is obtained. A substitution step is conducted, wherein a carbon dioxide is introduced into the intermediate solution so as to obtain the multi-substituted acrylic acid compound.
Synthesis of Trisubstituted Acrylic Acids through Nickel-Catalyzed Carbomagnesiation of Alkynes and Carbon Dioxide Fixation
Hung, Chen-Hsun,Santhoshkumar, Rajagopal,Chang, Yu-Che,Cheng, Chien-Hong
supporting information, p. 6924 - 6928 (2018/11/23)
A nickel-catalyzed synthesis of trisubstituted acrylic acids from alkynes, Grignard reagents, and CO2 is reported. The reaction proceeds through carbomagnesiation of the alkyne with Grignard reagent followed by carboxylation with CO2 under mild reaction conditions in short time. Various unsymmetrical alkynes were transformed into the corresponding acid products in good yields with high stereoselectivity.
The Development of a Stereoselective Method for the Synthesis of Tetrasubstituted Derivatives of α,β-Unsaturated Carboxylic Acids
Rzymkowski, Jan,Pi?tek, Anna
, p. 665 - 673 (2016/09/21)
Alkenes possessing four different carbon-linked substituents are the main structural motif of many biologically active compounds. The derivatives of (2E)-3-(3-methoxyphenyl)-2-methylpent-2-enoic acid ((E)-2c) are suitable precursors for the synthesis of Tapentadol, a novel centrally acting analgesic. It was found that the Ni-carbometallation reaction of disubstituted alkyne 8 with CO2and an Et2Zn allows for efficient and practical preparation of (E)-2c as a single (E)-regioisomer in 89% of isolated yield. The influence of the size of the aliphatic substituent of alkyne and the steric hindrance of the organozinc reagent on stereochemical course of the carbometallation reaction was evaluated. Finally, air-stable Ni(dme)Cl2was proposed as an alternative to widely used Ni(cod)2catalyst.
Copper-Catalyzed Carboxylation of Alkenylzirconocenes with Carbon Dioxide Leading to α,β-Unsaturated Carboxylic Acids
Wang, Sheng,Shao, Peng,Chen, Chao,Xi, Chanjuan
supporting information, p. 5112 - 5115 (2015/11/03)
A variety of alkenylzirconocenes were efficiently carboxylated by CO2 utilizing the (IMes)CuCl catalyst yielding the corresponding α,β-unsaturated carboxylic acids in good yields. This reaction could be carried out in a one-pot operation via sequential carbozirconation of alkynes and carboxylation using CO2 as starting materials under room temperature.
