(11b R )‐4‐Hydroxy‐2,6‐bis[2,4,6‐tris(1‐methylethyl)phenyl]‐dinaphtho[2,1‐ d :1′,2′‐ f ][1,3,2]dioxaphosphepin‐4‐oxide, [( R )‐ TRIP ] & (11b S )‐4‐Hydroxy‐2,6‐bis[2,4,6‐tris(1‐methylethyl)phenyl]‐dinaphtho[2,1‐ d : 1′,2′‐ f ][1,3,2]dioxaphosphepin‐4‐oxide, [( S )‐TRIP]

(11bR)-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethylphenyl]-dinaphtho[2,1-d: 1′,2′-f][1,3,2]dioxaphosphepin-4-oxide [791616-63-2] C50H57O4P (MW 752.96) InChI = 1S/C50H57O4P/c1-27(2)35-23-39(29(5)6)45(40(24-35)30(7)8)43-21-33-17-13-15-19-37(33)47-48-38-20-16-14-18-34(38)22-44(50(48)54-55(51,52)53-49(43)47)46-41(31(9)10)25-36(28(3)4)26-42(46)32(11)12/h13-32H,1-12H3,(H,51,52) InChIKey = AGQAQYPGJDBIQR-UHFFFAOYSA-N Solubility: soluble in dichloromethane, dioxane, toluene, and methanol. Form Supplied in: white crystalline solid. Preparative Methods: most preparative methods used for chiral phosphoric acid catalysts were followed in analogy to those developed by Akiyama1 and Uraguchi2 that follow the original substituted BINOL synthesis of Wipf3 from (R)-BINOL (3), as described in eq 1.4 Purification: following phosphate formation it is very important that the hydrolysis product is carefully stirred with hydrochloric acid solution to make sure that the product is not contaminated with salts or heavy metal impurities from earlier steps in the synthesis. The dichloromethane extract is then dried over anhydrous magnesium sulfate, concentrated, and then recrystallized from acetonitrile. Handling, Storage, and Precautions: while no major hazards with the handling of (R)- or (S)-TRIP are known, these reagents should be handled with the customary precautions used for other laboratory chemicals. (11bS)-4-Hydroxy-2,6-bis[2,4,6-tris(1-methylethyl)phenyl]-Dinaphtho[2,1-d: 1′,2′-f][1,3,2]dioxaphosphepin-4-oxide [874948-63-7] C50H57O4P (MW 752.96) InChI = 1S/C50H57O4P/c1-27(2)35-23-39(29(5)6)45(40(24-35)30(7)8)43-21-33-17-13-15-19-37(33)47-48-38-20-16-14-18-34(38)22-44(50(48)54-55(51,52)53-49(43)47)46-41(31(9)10)25-36(28(3)4)26-42(46)32(11)12/h13-32H,1-12H3,(H,51,52) InChIKey = AGQAQYPGJDBIQR-UHFFFAOYSA-N Solubility: soluble in dichloromethane, dioxane, toluene, and methanol. Form Supplied in: white crystalline solid. Preparative Methods: preparative methods used (S)-TRIP are in direct analogy to those described above for (R)-TRIP. These methods were developed by Akiyama1 and Uraguchi2 that follow the original substituted BINOL synthesis of Wipf3 from (S)-BINOL (3), as described in eq 2.4