Copper-catalyzed enantioselective allylic cross-coupling with alkylboranes was written by Hojoh, Kentaro;Shido, Yoshinori;Nagao, Kazunori;Mori, Seiji;Ohmiya, Hirohisa;Sawamura, Masaya. And the article was included in Tetrahedron in 2015.Name: (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl This article mentions the following:
Nonracemic alkenes such as (S)-3,4-(MeO)2C6H3(CH2)3CH(CH2CH2Ph)CH:CH2 and allylic silanes such as (S)-Me(CH2)7CH(SiMe2Ph)CH:CH2 were prepared by enantioselective SN2′-type allylic substitution reactions of (Z)-allylic chlorides such as (Z)-PhCH2CH2CH:CHCH2Cl and (Z)-PhMe2SiCH:CHCH2Cl with alkylboranes generated from terminal alkenes such as 1-allyl-3,4-dimethoxybenzene and 1-octene and the dimer of 9-borabicyclo[3.3.1]nonane in the presence of CuOTf•0.5PhMe and nonracemic biaryldiphosphine ligands using potassium methanolate or ethanolate in 1,4-dioxane/CH2Cl2 or THF/CH2Cl2 mixtures Using copper catalysts, enantioenriched chiral products containing tertiary or quaternary carbon stereogenic centers branched with functionalized sp3-alkyl groups were prepared; various functional groups (acetals, esters, silyl ethers, phthalimide) were tolerated. The wide availability of alkylboranes by hydroboration of alkenes is an attractive feature of these transformations. A reaction pathway involving addition and elimination of a neutral alkylcopper(I) species with the allyl chloride substrate is proposed. In the experiment, the researchers used many compounds, for example, (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9Name: (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl).
(R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl (cas: 352655-61-9) belongs to chiral phosphine ligands. Generally, the efficiency of nucleophilic phosphine catalysis often depends on the nature of the tertiary phosphine. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Name: (R)-(-)-2,2′-Bis[di(3,5-di-t-butyl-4-methoxyphenyl)phosphino]-6,6′-dimethoxy-1,1′-biphenyl
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis