Meng, Fanke;Haeffner, Fredrik;Hoveyda, Amir H. published 《Diastereo- and enantioselective reactions of bis(pinacolato)diboron, 1,3-enynes, and aldehydes catalyzed by an easily accessible bisphosphine-Cu complex》 in 2014. The article was appeared in 《Journal of the American Chemical Society》. They have made some progress in their research.Reference of (R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl The article mentions the following:
Catalytic enantioselective multicomponent processes involving bis(pinacolato)diboron B2(pin)2, 1,3-enynes RCCCH:CH2 (R = Ph, aryl, 3-thienyl, 1-cyclohexenyl, TIPSOCMe2, Et3Si), and aldehydes R1CHO (R1 = aryl, 3-benzo[b]thienyl, cinnamyl, cyclohexenyl, PhCH2CH2) resulting in chiral bis(homopropargyl) diols R1CH(OH)CH(CH2OH)CCR are disclosed; the resulting compounds contain a primary C-B(pin) bond, as well as alkyne- and hydroxyl-substituted tertiary carbon stereogenic centers. A critical feature is the initial enantioselective Cu-B(pin) addition to an alkyne-substituted terminal alkene. This and other key mechanistic issues have been investigated by DFT calculations Reactions are promoted by the Cu complex of a com. available enantiomerically pure bis-phosphine and are complete in 8 h at ambient temperature; products are generated in 66-94% yield (after oxidation or catalytic cross-coupling), 90:10 to >98:2 diastereomeric ratio, and 85:15-99:1 enantiomeric ratio. Aryl-, heteroaryl-, alkenyl-, and alkyl-substituted aldehydes and enynes can be used. Utility is illustrated through catalytic alkylation and arylation of the organoboron products as well as applications to synthesis of fragments of tylonolide and mycinolide IV.(R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl (cas: 1365531-84-5) were involved in the experimental procedure.
(R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl(cas: 1365531-84-5) is a compound of chiral-phosphine-ligands. At present, the synthesis of new chiral phosphines designed specifically for nucleophilic organocatalysis remains a significant challenge.Reference of (R)-2,2′-Bis[bis(3,5-trifluoromethylphenyl)phosphino]-4,4′,6,6′-tetramethoxy)-1,1′-biphenyl
Reference:
Phosphine ligand,
Chiral phosphines in nucleophilic organocatalysis