134996-34-2Relevant academic research and scientific papers
An aqueous and recyclable copper(i)-catalyzed route to α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols
Watile, Rahul A.,Biswas, Srijit,Samec, Joseph S. M.
supporting information, p. 3176 - 3179 (2013/11/06)
A highly efficient one-step copper(i)-catalyzed method for the synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols in aqueous media is described. A variety of α-sulfenylated carbonyl compounds can be synthesized in good to excellent yields. The catalyst has been successfully recycled up to 4 times without any loss of activity in an aqueous medium.
Atom-efficient gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols: Substrate scope and experimental and theoretical mechanistic investigation
Biswas, Srijit,Dahlstrand, Christian,Watile, Rahul A.,Kalek, Marcin,Himo, Fahmi,Samec, Joseph S. M.
supporting information, p. 17939 - 17950 (2014/01/17)
Gold(I)-chloride-catalyzed synthesis of α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols showed a wide substrate scope with respect to both propargylic alcohols and aryl thiols. Primary and secondary aromatic propargylic alcohol
A gold(I)-catalyzed route to α-sulfenylated carbonyl compounds from propargylic alcohols and aryl thiols
Biswas, Srijit,Samec, Joseph S. M.
supporting information; experimental part, p. 6586 - 6588 (2012/07/28)
A one-step atom efficient gold(i)-catalyzed route to α-sulfenylated ketones and aldehydes from propargylic alcohols and aryl thiols is described.
Amino-protecting groups subject to deblocking under conditions of nucleophilic addition to a Michael acceptor. Structure-Reactivity studies and use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) group
Carpino, Louis A.,Philbin, Michael
, p. 4315 - 4323 (2007/10/03)
A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael acceptors showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > C6H5SO > C6H4NO2-p. The reactivity of the nucleophile (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. β- Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.
A Novel Synthesis of 3,4-Dihydro-2H-1-benzothiopyrans. Acid-Catalyzed Intermolecular Cycloaddition of Acetylenic Alcohols with Arenethiols
Ishino, Yoshio,Masaoka, Toshihiro,Hirashima, Tsuneaki
, p. 1185 - 1188 (2007/10/02)
Reaction of the acetylenic alcohols with arenethiols in the presence of p-toluenesulfonic acid (p-TsOH) gave 3,4-dihydro-2H-1-benzothiopyrans (thiochromans) in good to excellent yields, the reaction of which may involve intermolecular cycloaddition via ca
