13733-59-0Relevant academic research and scientific papers
Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement
Kim, Hanbyul,Jang, Jiwon,Shin, Seunghoon
supporting information, p. 20788 - 20795 (2020/11/27)
A gold(I)-catalyzed enantioselective thioallylation of propiolates with allyl sulfides is described. The key mechanistic element is a sulfonium-induced Claisen rearrangement which helps minimize the allyl dissociation and render higher enantioselectivity. This protocol features remarkable scope of the allyl moiety, allowing enantiocontrolled synthesis of all-carbon quaternary centers, and exhibits exceptional functional group compatibility with many Lewis bases and π-bonds. This intermolecular variant of Claisen rearrangement forges both C-S and C-C bonds concomitantly, providing efficient access to interesting optically active organosulfur compounds which can be transformed further through the vinyl sulfide as a functional handle. The rate of the reaction was zeroth order with respect to allyl sulfides, which suggested a reversible inhibition, providing a resting state for the catalyst. The Hammett plot displayed a correlation with σp values, suggesting a turnover-limiting sigmatropic rearrangement where decreased electron-density on sulfur accelerated the rearrangement.
CARBON MONOXIDE-RELEASING MOLECULES TRIGGERED BY PHYSIOLOGICAL STIMULI
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Paragraph 0172; 0173; 0174; 0179, (2019/02/25)
The present invention generally relates to carbon monoxide releasing compounds and compositions, and their use as carbon monoxide prodrugs.
Cyclopropanation of active methylene compounds with β-alkoxycarbonyl vinylsulfonium salts
Guo, Shenquan,Zhang, Niuniu,Tang, Xiangzheng,Mao, Zhifeng,Zhang, Xuejing,Yan, Ming,Xuan, Yining
supporting information, p. 406 - 408 (2018/09/25)
An efficient synthesis of β-alkoxycarbonyl vinylsulfonium salts had been developed. Their reaction with indene-1,3-diones and other active methylene compounds provided cyclopropane carboxylates in good yields. A tentative reaction mechanism was proposed.
Reaction of Arynes with Vinyl Sulfoxides: Highly Stereospecific Synthesis of ortho-Sulfinylaryl Vinyl Ethers
Li, Yuanming,Studer, Armido
, p. 666 - 669 (2017/02/10)
The reaction of in situ generated arynes with aryl vinyl sulfoxides provides ortho-arylsulfinylaryl vinyl ethers via aryne σ-bond insertion into the S-O-bond and concomitant stereospecific S-O-vinyl migration. The cascade allows preparing di- or trisubsti
Facile synthetic method for the preparation of dithioacetals by the double conjugate addition of acetylenes bearing electronwithdrawing groups with thiols
Kuroda, Hirofumi,Tomita, Ikuyoshi,Endo, Takeshi
, p. 1539 - 1543 (2007/10/03)
β, β-Bis(alkylmercapto)propionates were obtained by the reaction of methyl propiolates with 2 equiv. of mercaptanes in the presence of tri-n-butylphosphine in high yield. The corresponding dithioacetals could be also obtained by the conjugate addition of mercaptanes toward methyl β-alkylmercaptoenoates, in which, tri-n-butylphosphine also catalyzed the addition of thiols.
Alumina-Catalyzed Addition of Thiols to Methyl Propiolate
Kodomari, Mitsuo,Saitoh, Goroh,Yoshitomi, Suehiko
, p. 3485 - 3487 (2007/10/02)
The addition of thiols to methyl propiolate was remarkably accelerated in the presence of alumina to give the Z-isomer of the 1:1 adducts stereoselectively, in which alumina acts as a bifunctional catalyst of acid and base.
STEREOSPECIFIC VINYL SUBSTITUTIONS OCCURRING BY FREE RADICAL ADDITION-ELIMINATION
Russell, Glen A.,Ngowiwatchai, Preecha
, p. 4975 - 4978 (2007/10/02)
The free radical chain reaction between cyclohexyl-HgCl and (E) or (Z) MeO2CCH=CHSnBu3, MeO2CCH=CHI, or ClCH=CHHgCl forms MeO2CCH=CHC6H11 or ClCH=CHC6H11 in a stereospecific manner with retention of stereochemistry.
Stereoselective Addition Reaction of Allylic Sulfides to Acetylenic Esters: E/Z Stereochemical Variations by Lewis Acid
Hayakawa, Kenji,Kamikawaji, Yoshimasa,Wakita, Akemi,Kanematsu, Ken
, p. 1985 - 1989 (2007/10/02)
The Lewis acid catalyzed addition reactions of allylic sulfides to methyl propiolate (MP) and dimethyl acetylenedicarboxylate (DMAD) have been investigated.The stereochemical outcome is considerably influenced by the Lewis acid.While the AlCl3-catalyzed r
