10277-56-2Relevant articles and documents
Stereo- and regioselective thiolysis of 1,2-epoxides in water
Movassagh, Barahman,Soleiman-Beigi, Mohammad
, p. 3239 - 3244 (2007)
A simple, efficient, stereoselective, and highly regioselective procedure for the synthesis of β-hydroxy sulfides by thiolysis of various 1,2-epoxides in water as a solvent, using no catalyst and under very mild conditions, is described. Copyright Taylor
Regioselective reaction of epoxides with disulfides using Zn/AlCl 3 system: A simple synthesis of β-hydroxy sulfides
Movassagh,Sobhani,Kheirdoush,Fadaei
, p. 3103 - 3108 (2003)
Epoxides are regioselectively cleaved by zinc thiolate intermediate, generated from disulfides in the presence of Zn/AlCl3 system, to afford high yields of the corresponding β-hydroxy sulfides.
Enantioselective S?H Insertion Reactions of α-Carbonyl Sulfoxonium Ylides
Burtoloso, Antonio C. B.,Farrar, Elliot H. E.,Grayson, Matthew N.,Leveille, Alexandria N.,Mattson, Anita E.,Momo, Patrícia B.
, p. 15554 - 15559 (2020)
The first example of enantioselective S?H insertion reactions of sulfoxonium ylides is reported. Under the influence of thiourea catalysis, excellent levels of enantiocontrol (up to 95 percent ee) and yields (up to 97 percent) are achieved for 31 examples
Efficient, eco-friendly and regioselective method for thiolysis of 1,2-epoxides with diaryl disulfides in the presence of Zn/Bi(TFA) 3-TBPB or Zn/Bi(OTf)3-TBPB
Khosropour, Ahmad R.,Khodaei, Mohammad M.,Ghozati, Kazem
, p. 572 - 576 (2005)
Diaryl disulfides undergo regioselective ring-opening of 1,2-epoxides in the presence of zinc powder and 3-4 mol-% of bismuth(III) trifluoroacetate or 1 mol-% of bismuth(III) triflate in molten tetrabutylphosphonium bromide (TBPB) to afford the correspond
Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
Wang, Shun,Cheng, Bei-Yi,Sr?en, Matea,K?nig, Burkhard
supporting information, p. 7524 - 7531 (2020/08/05)
The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.
N-Benzoyl- L -Threonine-Isopropyl-Ester-Mediated Crystallization-Induced Dynamic Resolution of α-Bromo Arylacetates for the Asymmetric Synthesis of α-Thio and α-Oxy Arylacetates
Park, Kon Ji,Kim, Yelim,Lee, Myung-Su,Park, Yong Sun
, p. 1645 - 1652 (2015/10/05)
N-Benzoyl-L-threonine-isopropyl-ester-mediated crystallization-induced dynamic resolution (CIDR) of configurationally labile α-bromo arylacetates has been investigated. The CIDR was successfully used for the asymmetric preparation of these compounds with up to 98:2 dr, under solution and solvent-free conditions. Subsequent nucleophilic substitution reactions with sulfur and oxygen nulceophiles gave α-thio and α-oxy arylacetates with up to 98:2 dr. The method was further developed for the preparation of highly enantioenriched 2-phenylthio-2-arylethanols with up to 97:3 er, and 1,4-benzoxazin-3-ones with up to 94:6 er.
