High Efficiency and Enantioselectivity in the Rh-Catalyzed Conjugate Addition of Arylboronic Acids Using Monodentate Phosphoramidites was written by Boiteau, Jean-Guy;Minnaard, Adriaan J.;Feringa, Ben L.. And the article was included in Journal of Organic Chemistry in 2003.Related Products of 252288-04-3 This article mentions the following:
A very fast reaction rates and high enantioselectivities were reached in the rhodium-catalyzed arylboronic acid addition to cyclic enones using a monodentate phosphoramidite ligand. Monodentate N,N-R2-phosphoramidous esters of (S)-1,1′-binaphthyl-2,2′-diol and (S)-octahydro-1,1′-binaphthyl-2,2′-diol (L1-L4) were prepared by reaction of corresponding diol with PCl3 followed by amination with NHR2 (R = Me, Et). Asym. conjugate addition of arylboronic acids ArB(OH)2 (Ar = Ph, 2-FC6H4, 3-MeOC6H4, 3-MeC6H4 4-MeC6H4) to 2-cyclohexenone, 2-cyclopentanone, 2-cycloheptenone and 5,6-dihydro-2-pyranone in the presence of Rh(acac)(C2H4)2/L4 (mol. ratio 1:2.5) gave corresponding 3-arylcycloalkanones and 4-phenyltetrahydro-2-pyranone with ee values > 96% (L4 = (S)-octahydro-1,1′-binaphthyl-2,2′-diyl N,N-diethylphosphoramidite). Temperature-dependent studies show that monodentate phosphoramidites form stable complexes with metals and can induce high enantioselectivities even at elevated temperatures in polar solvents. 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: 252288-04-3Related Products of 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. Phosphine-catalyzed asymmetric reactions are now powerful and versatile tools for the construction of C–C, C–N, C–O, and C–S bonds and for the syntheses of functionalized carbocycles and heterocycles. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Related Products of 252288-04-3
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis