(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Name: (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine
The long-arm effect: influence of axially chiral phosphoramidite ligands on the diastereo- and enantioselectivity of the tandem 1,4-addition/fluorination was written by Wang, Lian;Meng, Wei;Zhu, Chuan-Le;Zheng, Yan;Nie, Jing;Ma, Jun-An. And the article was included in Angewandte Chemie, International Edition in 2011.Name: (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine This article mentions the following:
Alkylidene-substituted β-aryl β-ketoesters undergo asym. tandem Michael addition and electrophilic fluorination in reaction with dialkylzinc compounds and N-fluorobenzenesulfonimide, catalyzed by copper(II) triflate, modified with axial chiral 1,1′-binaphthalene 2,2′-phosphoramidite monodentate ligands QO2PNR32 (1a–r, Q = 3,3′-diaryl-1,1′-binaphthalene-2,2-diyl, R3 = Me, Et, iPr, Bu), yielding α-fluoro-β-ketoesters I (3a–v, R = H, 4-MeO, 3-Me, 2-Me, 4-Cl, 4-Br; R1 = Et, Me, n-Pr, Bu; R2 = Ph, 2-MeOC6H4, 3-MeOC6H4, 4-MeOC6H4, 4-CF3C6H4, 2-naphthyl, 2-furyl, 2-thienyl)with high yields and >85% ee. The variety of 3,3′-disubstituted chiral phosphoramidites were evaluated, the 4-biphenylyl and 4-(2-naphthyl)phenyl substituents provided optimal chiral induction, 75-90%. N-Substituents of the phosphoramidites 1 play a minor role in induction, the diethylamino group as NR32 being optimal. In the experiment, the researchers used many compounds, for example, (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3Name: (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine).
(11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 252288-04-3) belongs to chiral phosphine ligands. Thousands of arylphosphines have been used as chiral ligands for metal-catalyzed asymmetric reactions. Chiral phosphine catalysts: Nucleophilic phosphine catalysis often involves the formation of Lewis adducts, namely phosphonium (di)enolate zwitterions, as reaction intermediates.Name: (11bS)-N,N-Diethyldinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis