64329-89-1Relevant academic research and scientific papers
Copper-Photocatalyzed Contra-Thermodynamic Isomerization of Polarized Alkenes
Bouillon, Jean-Philippe,Brégent, Thibaud,Poisson, Thomas
, p. 7688 - 7693 (2020/10/09)
The contra-thermodynamic isomerization of α- and β-substituted cinnamate derivatives catalyzed by the Cu(OAc)2/rac-BINAP complex under blue light irradiation is reported. The use of an oxazolidinone template, which favored the complexation of the copper catalyst to the substrate, allowed the E → Z isomerization of the catalytically formed chromophore under simple and robust reaction conditions in good to excellent ratios. The mechanism of this process based on the transient formation of a chromophore was also studied.
Highly Efficient Enantioselective Synthesis of Chiral Sulfones by Rh-Catalyzed Asymmetric Hydrogenation
Yan, Qiaozhi,Xiao, Guiying,Wang, Ying,Zi, Guofu,Zhang, Zhanbin,Hou, Guohua
, p. 1749 - 1756 (2019/01/25)
A highly efficient and enantioselective Rh-(R,R)-f-spiroPhos complex catalyzed hydrogenation of a series of unsaturated sulfones has been developed. With Rh-(R,R)-f-spiroPhos catalyst under mild conditions, not only the asymmetric hydrogenation of both the 3,3-diaryl and exocyclic α,β-unsaturated sulfones was first realized with up to 99.9% ee but also 3-alkyl-3-aryl and benzo[b]thiophene-1,1-dioxides were successfully hydrogenated to the corresponding chiral sulfones with excellent enantioselectivities (up to 99.4% ee) regardless of the steric hindrance, electronic property, and geometry of the substrates. Moreover, this reaction offers a route to (S)-(+)-ar-turmerone as a spice flavor, which is an important synthetic intermediate of pharmaceuticals.
An enantioselective approach to the preparation of chiral sulfones by ir-catalyzed asymmetric hydrogenation
Peters, Byron K.,Zhou, Taigang,Rujirawanich, Janjira,Cadu, Alban,Singh, Thishana,Rabten, Wangchuk,Kerdphon, Sutthichat,Andersson, Pher G.
, p. 16557 - 16562 (2015/01/09)
Several chiral sulfonyl compounds were prepared using the iridium catalyzed asymmetric hydrogenation reaction. Vinylic, allylic and homoallylic sulfone substitutions were investigated, and high enantioselectivity is maintained regardless of the location of the olefin with respect to the sulfone. Impressive stereoselectivity was obtained for dialkyl substitutions, which typically are challenging substrates in the hydrogenation. As expected, the more bulky Z-substrates were hydrogenated slower than the corresponding E isomers, and in slightly lower enantioselectivity.
