(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine
2H-quadrupolar coupling-based analysis of stereochemical and regiochemical memory in the Pd-catalyzed allylic alkylation of iso-cinnamyl type substrates employing the chiral monophosphine ligands “MOP” and “MAP” was written by Gouriou, Laure;Lloyd-Jones, Guy C.;Vyskocil, Stepan;Kocovsky, Pavel. And the article was included in Journal of Organometallic Chemistry in 2003.Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine This article mentions the following:
The reaction of isocinnamyl acetate with NaC(Me)(CO2Me)2, catalyzed by Pd-MOP (MOP = 2-methoxy-2′-diphenylphosphino-1,1′-binaphthalene) is known to proceed with a regiochem. memory effect that results in the predominant generation of the branched alkylation product. The analogous reaction employing MAP as ligand (MAP = 2-N,N-dimethylamino-2′-diphenylphosphino-1,1′-binaphthalene) proceeds with normal regioselectivity to generate predominantly the linear isomer of product. A 2H-NMR based anal., employing quadrupolar coupling in a chiral liquid crystal matrix, has been developed to facilitate the simultaneous study of the regiochem. and stereochem. outcome of the reaction of both enantiomers of iso-cinnamyl ester substrates in 2H-labeled but racemic samples. The anal. allows the comparison of relative rates of two competing isomerization processes occurring in the π-allyl intermediates in the Pd-catalyzed reaction, one of which facilitates asym. induction, the other resulting in loss of regiochem. memory. It is demonstrated that the two processes are partially coupled and that this then limits the attainment of high global enantiomeric excess in the branched product to reactions that proceed with low regiochem. retention. A key factor for the observation of high regiochem. memory is found to be the nucleophilicity of the malonate anion and the electrophilicity of the Pd-π-allyl intermediate with reduction in the reactivity of either partner resulting in the onset of substantial loss of memory. In the experiment, the researchers used many compounds, for example, (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine).
(S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine (cas: 134484-36-9) belongs to chiral phosphine ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge. Over the last decade, however, and especially since 2005, considerable progress has been made in asymmetric phosphine catalysis.Safety of (S)-(2′-Methoxy-[1,1′-binaphthalen]-2-yl)diphenylphosphine
Referemce:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis