Otomaru, Yusuke et al. published their research in Organic Letters in 2005 | CAS: 252288-04-3

(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. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Synthetic Route of C24H22NO2P

C2-symmetric bicyclo[3.3.1]nonadiene as a chiral ligand for rhodium-catalyzed asymmetric arylation of N-(4-nitrobenzenesulfonyl)arylimines was written by Otomaru, Yusuke;Tokunaga, Norihito;Shintani, Ryo;Hayashi, Tamio. And the article was included in Organic Letters in 2005.Synthetic Route of C24H22NO2P This article mentions the following:

Nonracemic (+)-2,6-diphenylbicyclo[3.3.1]-2,6-nonadiene (I) is prepared in two steps from 2,6-bicyclo[3.3.1]nonanedione; complex {Rh[(+)-I]2Cl}2 (II) is an effective catalyst for the addition of arylboroxines [(R)BO]3 (R = Ph, 4-ClC6H4, 4-MeOC6H4, 3-MeOC6H4, 2-MeC6H4) to N-(4-nitrobenzenesulfonyl)imines R1C(:NNs)H (R1 = Ph, 4-ClC6H4, 4-BrC6H4, 4-MeO2CC6H4, 4-MeOC6H4, 2-MeC6H4, 1-naphthyl, 2-thienyl; Ns = 4-O2NC6H4SO2) to yield nonracemic diarylmethylamines RCH(NHNs)R1 in 94-99% yields and in 95-99% ee. Addition of phenyllithium and cerium chloride to 2,6-bicyclo[3.3.1]nonanedione followed by phosphorus oxychloride-mediated elimination yields racemic I which is resolved by chiral HPLC to yield (+)-I; reaction of (+)-I with [Rh(C2H4)2Cl]2 yields II. Catalysts generated in situ from bisphosphines and [Rh(C2H4)2Cl]2 are ineffective for the enantioselective addition reaction; catalysts generated from either a binaphthyldiol phosphoramidite or nonracemic bicyclic dienes and [Rh(C2H4)2Cl]2 catalyze the enantioselective addition but with lower enantioselectivities than II. Deprotection of the 4-nitrobenzenesulfonyl group with benzenethiol and potassium carbonate in DMF yields the free diarylmethylamines in two cases with no loss of enantioselectivity. 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: 252288-04-3Synthetic Route of C24H22NO2P).

(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. Although many reactions require more nucleophilic trialkylphosphines as catalysts, only a few chiral trialkylphosphines are available. Most of these phosphines are acyclic, usually possess low nucleophilic activity, and generally display poor enantioselectivities for phosphine organocatalysis. Synthetic Route of C24H22NO2P

Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis