13023-53-5Relevant articles and documents
Synthesis and reactivity of α-sulfenyl-β-chloroenones, including oxidation and Stille cross-coupling to form chalcone derivatives
Kearney, Aoife M.,Murphy, Linda,Murphy, Chloe C.,Eccles, Kevin S.,Lawrence, Simon E.,Collins, Stuart G.,Maguire, Anita R.
supporting information, (2021/05/04)
The synthesis of a range of novel α-sulfenyl-β-chloroenones from the corresponding α-sulfenylketones, via a NCS mediated chlorination cascade, is described. The scope of the reaction has been investigated and compounds bearing alkyl- and arylthio substituents have been synthesised. In most instances, the Z α-sulfenyl-β-chloroenones were formed as the major products, while variation of the substituent at the β-carbon position led to an alteration in stereoselectivity. Stille cross-coupling with the Z α-sulfenyl-β-chloroenones led to selective formation of Z sulfenyl chalcones, while the E α-sulfenyl-β-chloroenones did not react under the same conditions. Oxidation of the Z α-sulfenyl-β-chloroenones was followed by isomerisation, leading to the E α-sulfinyl-β-chloroenones. Stille cross-coupling with the E α-sulfinyl-β-chloroenones produced the E sulfinyl chalcones. Either the E or Z sulfinyl chalcones can be obtained by altering the sequence of oxidation and Stille cross-coupling.
Tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols
Biswas, Srijit,Watile, Rahul A.,Samec, Joseph S. M.
supporting information, p. 2159 - 2163 (2014/03/21)
An efficient and highly atom-economical tandem Pd/Au-catalyzed route to α-sulfenylated carbonyl compounds from terminal propargylic alcohols and thiols has been developed. This one-step procedure has a wide substrate scope with respect to substituents at
Asymmetrische Katalysen, 58. Mitt.: Enantioselektive S-H- und C-H-Insertionen mit optisch aktiven Rh(II)- und Cu(II)-Katalysatoren
Brunner, Henri,Wutz, Konrad,Doyle, Michael
, p. 755 - 764 (2007/10/02)
The substrates for the S-H insertion reaction were azibutanone 2 and thiophenol 3.Methyl 2-diazo-3-oxo-heptane-caboxylate 26 was used as the substrate in an intramolecular C-H insertion.Both reactions were carried out enantioselectively in the presence of optically active rhodium(II) and copper(II) catalysts.For the S-H insertion optical inductions up to 13.8percentee and for the C-H insertion up to 14percentee were achieved.
