In 2019,Journal of the American Chemical Society included an article by Hong, Feng-Lin; Wang, Ze-Shu; Wei, Dong-Dong; Zhai, Tong-Yi; Deng, Guo-Cheng; Lu, Xin; Liu, Rai-Shung; Ye, Long-Wu. Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole. The article was titled 《Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles》. The information in the text is summarized as follows:
In the presence of Cu(MeCN)4PF6, N-propargyl vinylaryl ynamides such as I (Ts = 4-MeC6H4SO2) underwent diastereoselective cascade cyclization reactions via copper carbenes to yield cyclopropabenzoisoindoles such as II; when a nonracemic bisoxazoline ligand was used, the cyclopropabenzoisoindoles were prepared in 90:10-97:3 er. N-Propargyl aryl ynamides such as III underwent enantioselective cyclization reactions in the presence of Cu(MeCN)4PF6 and (R)- or (S)-Segphos to yield nonracemic indanopyrroles such as IV. Mechanistic studies revealed that donor/donor copper carbenes are involved in the 1,5-diyne cyclization reactions, in contrast to reactions of gold catalysts, and provides a novel method to generate donor/donor carbenes. The experimental process involved the reaction of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3Safety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole)
(S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole(cas: 210169-54-3) may be used for: rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes, stereoselective preparation of homoallylic alcohols via Ir-catalyzed stereoselective transfer hydrogenative crotylation of an allylic acetate with alcohols or aldehydesSafety of (S)-5,5′-Bis(diphenylphosphino)-4,4′-bi-1,3-benzodioxole
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis