Alexakis, Alexandre;Trevitt, Graham P.;Bernardinelli, Gerald published 《Tandem enantioselective conjugate addition: Electophile trapping reactions. Application in the formation of syn or anti aldols》 in 2001. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.SDS of cas: 201732-49-2 The article mentions the following:
2-Cyclohexen-1-one and 2-cyclohept-en-1-one underwent cupric triflate/phosphoramidate ligand catalyzed enantioselective addition of Et2Zn to give homochiral zinc enolate intermediates which were trapped by cleavage reactions with acetals and orthoesters to give alkoxy substituted and protected 1,3-dicarbonyl products, resp. Thus, reaction of 2-cyclohexen-1-one in CH2Cl2 containing cupric triflate and the phosphoramidate ligand I with Et2Zn at -30° for 30 min and then with Me2C(OMe)2 or HC(OMe)3 in the presence of F3B.OEt2 gave the trans-ethylcyclohexanones II and III, resp. Application of chiral acetals, e.g. diphenyldioxolanes IV (R = Ph, 1-propenyl), to this reaction enabled three contiguous stereocenters and two carbon-carbon bonds to be generated in a tandem, one-pot reaction to give aldol products, e.g. V (R = Ph, allyl). The experimental procedure involved many compounds, such as (11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine (cas: 201732-49-2) .
(11bS)-2,6-Dimethyl-N,N-bis(1-phenylethyl)dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine(cas: 201732-49-2) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.SDS of cas: 201732-49-2
Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis