56377-46-9Relevant academic research and scientific papers
Thioallenoates in catalytic enantioselective [2+2]-cycloadditions with unactivated alkenes
Conner, Michael L.,Wiest, Johannes M.,Brown, M. Kevin
, p. 3265 - 3271 (2019)
The application of thioallenoates to catalytic enantioselective [2+2]-cycloadditions with unactivated alkenes is reported. In many cases, the thioallenoates examined exhibit superior reactivity and selectivity compared to the allenic esters generally used in these cycloadditions.
Asymmetric isomerization of ω-hydroxy-α,β-unsaturated thioesters into β-mercaptolactones by a bifunctional aminothiourea catalyst
Fukata, Yukihiro,Okamura, Takaaki,Asano, Keisuke,Matsubara, Seijiro
supporting information, p. 2184 - 2187 (2014/05/06)
We present a novel methodology for the asymmetric synthesis of β-mercaptolactones via isomerization of ω-hydroxy-α,β- unsaturated thioesters by means of a bifunctional aminothiourea catalyst. The catalyst interacts with the substrate through the cooperati
Organocatalytic asymmetric oxy-Michael addition to a γ-hydroxy- α,β-unsaturated thioester via hemiacetal intermediates
Okamura, Takaaki,Asano, Keisuke,Matsubara, Seijiro
supporting information; experimental part, p. 5076 - 5078 (2012/07/02)
We report an asymmetric oxy-Michael addition to a γ-hydroxy-α, β-unsaturated thioester via hemiacetal intermediates in the presence of Cinchona-alkaloid-thiourea-based bifunctional organocatalysts. This method provides a novel enantioselective route to β-hydroxy carboxyl compounds, which in turn can be used to synthesize valuable chiral building blocks.
Cycloadditions, XXII Synthesis and Thermal Reaction of S-(Alkyl/Aryl)-2,3-butadienethioates
Himbert, Gerhard,Fink, Dieter
, p. 542 - 550 (2007/10/02)
While the S-alkyl- or S-phenyl-2,3-butadienethioates 4a-c are synthesized via the usual "Wittig ylide way", the corresponding 2-methyl-2,3-butadienethioates 9a-d and the 2-methyl-4,4-diphenyl-2,3-butadienethioates 9e,f are obtained by condensation of the allenic acids 7a,b with the thiols and thiophenols 8 in the presence of dicyclohexylcarbodiimide (DCC) and a catalytic amount of 4-dimethylaminopyridine (DMAP).In contrast to N- or O-phenyl 2,3-butadienamides or -esters, resp., the phenyl derivatives of 4 and 9 do not undergo the intramolecular Diels-Alder reaction, but by heating, all representatives of 4 only decompose, while 9a-d and 9e,f rearrange to 3-alkyl(aryl)thio-2-cyclobuten-1-ones 12a-d and to 3-arylthio-1-naphthols 14a,b, resp.Heating of the cyclobutenone 12d in the presence of N-methylaniline furnishes the 2-butenanilide 16.On reacting 1-phenylthio-1-propyne 17 with diphenylketene 18, the diphenylacetate 19 is isolated, where the naphthol derivative 14 a represents the ester moiety. - Keywords: S-(Alkyl/Aryl)-2,3-butadienethioates, 3-Alkyl(aryl)thio-2-cyclobuten-1-ones, 3-Arylthio-1-naphthols
