22956-11-2Relevant academic research and scientific papers
OPTICAL INDUCTION - IV Optical Induction by Using Homogeneous Catalyst
Ahuja, R. R.,Natu, A. A.,Gogte, V. N.
, p. 4743 - 4744 (1980)
Better optical induction during Michael addition has been achieved by using new homogeneous catalysts based on quinine and quinidine.
Catalyst-free chemoselective α-sulfenylation/β-thiolation for α,β-unsaturated carbonyl compounds
Huang, Xi,Li, Juan,Li, Xiang,Wang, Jiayi,Peng, Yanqing,Song, Gonghua
, p. 26419 - 26424 (2019/09/13)
A novel, efficient, catalyst-free and product-controllable strategy has been developed for the chemoselective α-sulfenylation/β-thiolation of α,β-unsaturated carbonyl compounds. An aromatic sulfur group could be chemoselectively introduced at α-or β-posit
SmI2-mediated reductive cyclization of β-arylthio ketones: A facile and diastereoselective synthesis of thiochroman derivatives
Mao, Hui,You, Bing-Xin,Zhou, Lie-Jin,Xie, Ting-Ting,Wen, Yi-Hang,Lv, Xin,Wang, Xiao-Xia
, p. 6157 - 6166 (2017/08/02)
SmI2-mediated reductive cyclization of β-arylthio ketones to generate thiochroman derivatives is not a generally observed process and the reported examples are limited to geminal disubstitution in the substrates. The results of the current stud
NMR and DFT Insight into the Synergistic Role of Bovine Serum Albumin–Ionic Liquid for Multicomponent Cascade Aldol/Knoevenagel–thia-Michael/Michael Reactions in One Pot
Thopate, Yogesh,Singh, Richa,Sinha, Arun K.,Kumar, Vikash,Siddiqi, Mohammad Imran
, p. 3050 - 3056 (2016/10/11)
The synergistic combination of two catalysts is an emerging strategy towards the formation of unprecedented complex molecules, and herein bovine serum albumin (BSA) and the neutral ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) are used together for the first time towards multiple C?C and C?S bond-formation reactions in one pot under metal-free, acid-free, and base-free conditions by merging two classical named reactions, that is, aldol condensation (AC) and thia-Michael addition (TMA) for the cascade chemoselective generation of β-aryl-β-sulfido carbonyl compounds from aliphatic ketones, aromatic aldehydes, and thiols. NMR spectroscopy and DFT calculations studies provided insight into the synergism, progress, and mechanism of the reaction, and control experiments highlighted that the single catalysts (BSA or IL) alone did not allow even the first AC step to proceed. Moreover this synergistic BSA–[bmim]Br catalytic system offers the step-economical synthesis of the anticoagulant warfarin through sequential aldol–Michael addition reactions and potent pyridine analogues through a Knoevenagel–Michael route. Besides, the recyclability of the catalytic system (up to 5 times) with the generation of water as a byproduct makes our one-pot protocol more economically efficient and synthetically attractive than traditional methods.
Thioboration of α,β-unsaturated ketones and aldehydes toward the synthesis of β-sulfido carbonyl compounds
Civit, Marc G.,Sanz, Xavier,Vogels, Christopher M.,Webb, Jonathan D.,Geier, Stephen J.,Decken, Andreas,Bo, Carles,Westcott, Stephen A.,Fernández, Elena
supporting information, p. 2148 - 2154 (2015/05/19)
Herein a direct β-sulfido carbonyl compound synthesis by the easy activation of RS-Bpin reagents with α,β-unsaturated ketones and aldehydes is reported. This convenient methodology can be performed at room temperature with no other additives. The key poin
Sonochemical synthesis of lithium fluoride nano cubic as an active and simple catalyst for thia-Michael addition process: Synthesis and structural characterization of β-aryl-β-mercapto ketones
Shobeiri, Zohreh,Pourayoubi, Mehrdad,Neas, Marek,Divjakovic, Vladimir,Babiak, Michal
, p. 245 - 255 (2015/02/19)
LiF nano cubic, with an average particle size of 21.6 nm, was synthesized sonochemically, using tetrabutylammonium fluoride as the fluoride source and characterized by SEM-EDX and XRD. This was applied, as a heterogeneous nano-catalyst, to synthesize some
Synthesis of β-sulfanyl ketones via a tandem rearrangement-conjugate addition reaction catalyzed by a Re(V)-oxo complex
Garst, Alyson E.,Badiceanu, Alexandra D.,Nolin, Kristine A.
supporting information, p. 459 - 461 (2013/02/23)
A method for synthesizing β-sulfanyl ketones via a tandem rearrangement and conjugate addition reaction has been developed. This methodology provides access to a range of β-sulfanyl ketones through the rearrangement of propargyl alcohols to the corresponding enones followed by the conjugate addition of unactivated thiols. The one-pot, tandem transformation is catalyzed by ReOCl3(OPPh3)(S(CH3)2) affording aryl and alkyl β-sulfanyl ketones in good to excellent yield.
E-factor minimized protocols for the polystyryl-BEMP catalyzed conjugate additions of various nucleophiles to α,β-unsaturated carbonyl compounds
Bonollo, Simona,Lanari, Daniela,Longo, Julie M.,Vaccaro, Luigi
supporting information; experimental part, p. 164 - 169 (2012/04/04)
Efficient protocols for the addition of carbon-, sulphur- and nitrogen-nucleophiles to α,β-unsaturated carbonyl compounds catalyzed by PS-BEMP have been reported. The adoption of solvent-free conditions (SolFC) was crucial for improving the efficiency of all the processes, while by using an organic reaction medium poor results were obtained. Addition reactions were performed by using equimolar amounts of reagents, and the products were isolated by simple filtration with the minimal amount of organic solvent. This approach allowed the E-factor, a measure of the waste of a reaction, to be minimized. Further waste minimization (95.7% compared to batch protocol) has been accomplished by defining a larger scale continuous-flow protocol operating under SolFC.
Conjugate addition of unactivated thiols to α,β-unsaturated ketones catalyzed by a bifunctional rhenium(V)-oxo complex
Peng, Allan,Rosenblatt, Ross,Nolin, Kristine
supporting information; experimental part, p. 2712 - 2714 (2012/07/14)
ReOCl3(OPPh3)(S(CH3)2) has been found to be an efficient bifunctional catalyst for the 1,4-addition of thiols to α,β-unsaturated ketones. The addition of thiophenol derivatives and alkyl thiols proceeds under mi
Ionic liquid catalysed reaction of thiols with α,β-unsaturated carbonyl compounds-remarkable influence of the C-2 hydrogen and the anion
Sarkar, Anirban,Roy, Sudipta Raha,Chakraborti, Asit K.
supporting information; experimental part, p. 4538 - 4540 (2011/06/22)
Hydrogen bond induced reactivity and selectivity control in the 1-butyl-3-methylimidazolium based ionic liquid catalysed reaction of thiols with α,β-unsaturated carbonyl compounds is reported with remarkable influence of the anion and the C-2 hydrogen in
