114140-96-4Relevant academic research and scientific papers
A direct catalyst-free and stereoselective sulfonylation of propargyl esters for efficient synthesis of (Z)-β-sulfonyl enoates in water
Jiang, Jun,Wu, Yundong,Wang, Ruijia,He, Yongzhao,Xu, Chonghui,Deng, Wei,Zeng, Zebing,Xiang, Jiannan
, p. 7895 - 7900 (2016)
Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, and environmentally benign reaction procedure without employing any ligand or additive is reported.
Regioselective and stereoselective sulfonylation of alkynylcarbonyl compounds in water
Li, Wenyi,Yin, Guoxing,Huang, Lei,Xiao, Yan,Fu, Zhimin,Xin, Xiu,Liu, Fang,Li, Zhizhang,He, Weimin
, p. 4879 - 4883 (2016)
With water as the reaction medium, an efficient protocol has been developed for the synthesis of Z-β-sulfonyl-α,β-unsaturated carbonyl products via water-promoted sulfonylation of alkynylcarbonyl compounds with sodium sulfinates. This strategy could effectively avoid the use of toxic organic solvents, catalysts and additives. This method features a wide substrate scope with a broad range of functional group tolerance, utilizes easily available starting materials, can be scaled-up, and is operationally simple.
Regio- and Stereoselective Hydrosulfonylation of Electron-Deficient Alkynes: Access to Both E- and Z-β-Sulfonyl-α,β-Unsaturated Carbonyl Compounds
Zhang, Wei,Johnson, Gabriel M.,Guan, Zhi,He, Yan-Hong
supporting information, p. 4562 - 4570 (2018/10/24)
A metal-free hydrosulfonylation of electron-deficient alkynes with sodium sulfinates or sulfinic acids to access both E- and Z-β-sulfonyl-α,β-unsaturated carbonyl compounds has been developed. We propose that this reaction via a hydroxylallene intermediate delivers the thermodynamically stable E isomer, or via a concerted termolecular AdE3 mechanism affords Z isomer. The stereoselectivity of addition (syn or anti) can be controlled by varying the sulfonyl sources and acidic buffer solutions. This protocol exhibits broad substrate scope for internal or terminal alkynes including various substituted ynones and alkynyl esters. This approach is mild, efficient, operationally simple and easy to be scaled-up. (Figure presented.).
A (Z)-sulfonyl dibutyl ester preparation method (by machine translation)
-
Paragraph 0032; 0033; 0034; 0035; 0036, (2016/10/17)
This invention relates to a kind of (Z)-sulfonyl dibutyl ester preparation method, the method is the ester compound acetylenic acid[...] compound and through the one-pot synthesis generating addition-elimination reaction, to obtain sulfonyl dibutyl ester; under mild conditions of the method, by one-pot reaction, high yield, high selectivity synthesis of (Z)-type sulfonyl enoic acid ester compound, and the operation is simple, environment friendly, and without need to add the catalyst, which is beneficial for industrial production. (by machine translation)
A Mild and Rapid Synthesis of (Z)-β-Sulfonyl Enoates from Sodium Sulfinates and Propargyl Esters
Jiang, Jun,Zou, Huaxu,Yi, Niannian,Wang, Ruijia,Zhang, Hao,Lan, Lixin,Xiang, Jiannan
, p. 1245 - 1250 (2016/12/27)
Water-promoted sulfonylation of propargyl esters leading to highly regioselective and stereoselective formation of (Z)-β-sulfonyl enoates in excellent yields, by a simple, mild, rapid and environmentally benign reaction procedure is reported.
Regio- and Stereoselective Hydrosulfonation of Alkynylcarbonyl Compounds with Sulfinic Acid in Water
Wu, Chao,Yang, Panpan,Fu, Zhimin,Peng, Yong,Wang, Xin,Zhang, Zuozhi,Liu, Fang,Li, Wenyi,Li, Zhizhang,He, Weimin
, p. 10664 - 10671 (2016/11/29)
We report the atom-economic and environmentally friendly synthesis of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds in water. The mechanism study reveals that the hydrosulfonylation of alkynylcarbonyl compounds with sulfinic acids proceeds via a mechanism that features a sulfinic acid molecule protonating an alkynyl motif to form the ethenium intermediate, which subsequently reacted with a sulfonyl anion to afford the desired products. The ethenium intermediate differentiated electronic and steric demands between the two substituents on the C≡C triple bond of the alkyne substrates to exhibit high regio- and stereoselectivity from a wide range of Z-β-sulfonyl-a,β-unsaturated carbonyl compounds.
One-pot synthesis of (Z)-β-sulfonyl enoates from ethyl propiolate
Downey, C. Wade,Craciun, Smaranda,Neferu, Ana M.,Vivelo, Christina A.,Mueller, Carly J.,Southall, Brian C.,Corsi, Stephanie,Etchill, Eric W.,Sault, Ryan J.
supporting information, p. 5763 - 5765 (2012/10/29)
β-Sulfonyl enoates may be synthesized through a one-pot two-step sequence from ethyl propiolate with good to excellent selectivity for the Z isomer. Trialkylamines catalyze thioconjugate additions of aryl thiols, and alkoxides catalyze the addition of ali
One-pot three-step thioconjugate addition-oxidation-Diels-Alder reactions of ethyl propiolate
Downey, C. Wade,Craciun, Smaranda,Vivelo, Christina A.,Neferu, Ana M.,Mueller, Carly J.,Corsi, Stephanie
supporting information, p. 5766 - 5768 (2012/11/06)
Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels-Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S-aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47% to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step-by-step.
Arylsulfonylpyrroles from reaction of tosylmethyl isocyanide (tosmic) with 3-arylsulfonyl acrylates as michael acceptors
Di Santo, Roberto,Costi, Roberta,Massa, Silvio,Artico, Marino
, p. 1801 - 1815 (2007/10/03)
Ethyl 3-(arylthio)acrylates did not react with α-alkali metalated tosylmethyl isocyanide (TosMIC) to afford 4-(arylthio)pyrrole-3-carboxylic acid ethyl esters. Oxidation of thioethers to sulfones generated reactive 3- (arylsulfonyl) acrylates, which promptly underwent cycloaddition with TosMIC in the presence of base giving ethyl 4-(arylsulfonyl)pyrrole-3-carboxylates. Contrary to expectation, the use of ethyl 3-(5-chloro-2- nitrophenylsulfonyl)acrylate led to ethyl ester of 5-tosylpyrrole-3- carboxylic acid instead of the expected ethyl 4-(5-chloro-2- nitrophenylsulfonyl)pyrrole-3-carboxylate.
