41103-85-9Relevant academic research and scientific papers
Asymmetric Induction in the Reaction of a Chiral Lithiated Sulphoxide and Aldehydes
House, Stewart,Jenkins, Paul R.,Fawcett, John,Russell, David R.
, p. 1844 - 1845 (1987)
Significant asymmetric induction has been observed in the reaction of 1-lithio-2-phenyl-1-(R)-p-tolylsulphinylethylene; the sense of this induction has been established by an X-ray structure on one of the products.
PhB(OH)2-Promoted Electrochemical Sulfuration-Formyloxylation of Styrenes and Selectfluor-Mediated Oxidation-Olefination
Zhao, Yulei,Guo, Xuqiang,Li, Shuai,Fan, Yuhang,Sun, Xuejun,Tian, Laijin
, p. 9140 - 9145 (2021/11/30)
We report a PhB(OH)2-promoted electrochemical sulfuration-formyloxylation reaction of styrenes employing commercially available thiophenols/thiols as thiolating agents. Specifically, metal catalysts and external chemical oxidants are not needed in the reaction for the formation of β-formyloxy sulfides, and these sulfides can be further converted to (E)-vinyl sulfones via the Selectfluor-mediated oxidation-olefination. Notably, on the basis of this electrochemical oxidation strategy, β-hydroxy sulfide, β-formyloxy sulfoxide, β-formyloxy sulfone, and (E)-vinyl sulfoxide can also be easily prepared.
Visible-light-induced selective synthesis of sulfoxides from alkenes and thiols using air as the oxidant
Cui, Huanhuan,Wei, Wei,Yang, Daoshan,Zhang, Yulong,Zhao, Huijuan,Wang, Leilei,Wang, Hua
supporting information, p. 3520 - 3524 (2017/08/15)
A highly selective synthesis of sulfoxides from alkenes and thiols was established by visible-light photoredox catalysis at room temperature. This metal-free transformation protocol, which uses inexpensive Rose Bengal as the photocatalyst and air as the green oxidant, opens a new door toward the facile and practical construction of sulfoxides.
(Diphenoxyphosphoryl)methyl p -tolyl sulfoxide: A new reagent for Z -selective synthesis of racemic and optically active vinyl sulfoxides
Midura, Wanda H.,Ewas, Ashraf M. Mohamed,Miko?ajczyk, Marian
, p. 535 - 540 (2016/04/05)
Racemic and optically active (+)-(S)-(diphenoxyphosphoryl)methyl p-tolyl sulfoxide were prepared and used as Horner olefination reagents. Their reaction with aromatic and aliphatic aldehydes afforded the corresponding racemic and enantiomeric α,β-unsatura
Stereoselective heck reactions with vinyl sulfoxides, sulfides and sulfones
Bachmann, Daniel G.,Wittwer, Christopher C.,Gillingham, Dennis G.
supporting information, p. 3703 - 3707 (2014/01/06)
We report the Heck cross-coupling of notoriously unreactive, but synthetically valuable olefins: vinyl sulfoxides, vinyl sulfones, and vinyl sulfides. Key findings include the importance of the sterically hindered (tri-tert-butyl)phosphine ligand and the unique effectiveness of triethylamine as the base. The method is general, E-selective, and can be used to synthesize disubstituted or trisubstituted olefins through simple adjustments of stoichiometry. Copyright
Metal-free, one-pot highly selective synthesis of (E)-vinyl sulfones and sulfoxides via addition-oxidation of thiols with alkynes
Xue, Qicai,Mao, Zhijie,Shi, Yan,Mao, Haibin,Cheng, Yixiang,Zhu, Chengjian
scheme or table, p. 1851 - 1854 (2012/04/23)
We have developed a highly selective one-pot method for the synthesis of (E)-vinyl sulfones and sulfoxides from thiols with terminal alkynes. The sulfones and sulfoxides could be obtained with excellent selectivity in good isolated yields. It is simple, e
Horner olefination reaction in organic sulfur chemistry and synthesis of natural and bioactive products
Mikolajczyk, Marian,Midura, Wanda H.,Mohamed Ewas, Ashraf M.,Perlikowska, Wieslawa,Mikina, MacIej,Jankowiak, Aleksandra
scheme or table, p. 313 - 325 (2009/04/06)
This article outlines the results of our work on the application of the Horner olefination reaction for the synthesis of unsaturated sulfur compounds. A general synthesis of racemic and optically-active α,β-unsaturated sulfoxides by the Horner reaction with α-sulfinylmethylphosphonates as olefination reagents is presented. We demonstrated how the structure of the phosphonate moiety may control the E- and Z-stereoselectivity in the above reaction. The use of racemic and optically-active α- sulfinylvinylphosphonates in tandem Michael addition/Horner olefination reaction leads to a wide range of carbocyclic and heterocyclic vinyl sulfoxides. In second part of this account a new strategy for the synthesis of functionalized cyclopentenones is briefly described. The synthesis and reactivity of 3-phosphorylmethyl-cyclopentenones is discussed as a platform for developing the synthesis of racemic rosaprostol, enantiomeric prostaglandin B1 methyl esters, enantiopure isoterreins, natural and unnatural neplanocin A and enantiomeric forms of phytoprostane B1 type I. Copyright Taylor & Francis Group, LLC.
Hydrotelluration and carbotelluration of acetylenic sulfoxides: Regio- and stereoselective preparation of α- and β-organotellurovinyl sulfoxides
Xu, Qing,Huang, Xian,Ni, Jun
, p. 2981 - 2984 (2007/10/03)
(Z)-β-Organotellurovinyl sulfoxides were synthesized via a highly regio- and stereoselective anti-hydrotelluration of acetylenic sulfoxides. α-Organotellurovinyl sulfoxides were obtained from a three component syn-carbotelluration reaction of acetylenic s
Studies on hydrozirconation of 1-alkynyl sulfoxides or sulfones and the application for the synthesis of stereodefined vinyl sulfoxides or sulfones
Huang, Xian,Duan, Dehui,Zheng, Weixin
, p. 1958 - 1963 (2007/10/03)
The hydrozirconation reaction of 1-alkynyl sulfoxides or sulfones with CP2Zr(H)Cl in THF at room temperature predominantly gave Z-β-zirconated vinyl sulfoxides or sulfones with excellent regioselectivity. Compared with 1-alkynyl sulfoxides, the hydrozirconation reaction of 1-alkynyl sulfones exhibits great synthetic potential, leading to the efficient preparation of Z-β-halovinyl sulfones, Z-β-sulfonyl α,β-unsaturated ketones, and Z-β-alkynyl vinyl sulfones. Although the reaction mechanisms are still not clear, the neighboring group participation of the sulfinyl or sulfonyl group may be playing an important role in this unique hydrozirconation reaction.
Stereospecific Grignard reactions of cholesteryl 1-alkenesulfinate esters: Application of the Andersen protocol to the preparation of non-racemic α,β-unsaturated sulfoxides
Strickler, Rick R.,Motto, John M.,Humber, Craig C.,Schwan, Adrian L.
, p. 423 - 430 (2007/10/03)
Enantiomerically enriched α,β-unsaturated sulfinate esters of (-)-cholesterol undergo stereospecific substitutions at sulfur when treated in benzene at 6°C with Grignard reagents. Sulfoxides with ees of 85-99.5% are obtained when enantiopure sulfinates are used. The substitution reactions proceed with inversion of sulfur configuration. Enantiomerically pure cholesteryl (E)-2-carbomethoxyethenesulfinate is not a suitable reactant under the Grignard reaction conditions. It is suggested that the ester group induces unwanted reactions significantly lowering both the yield and sulfur stereogenicity.
