S-3,3'-Bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate

Chemical Properties

Uses

• In the synthesis of 1,3-dioxolochroman skeletons by reacting 3-methyl-2-vinylindoles with ortho-quinone methides.
• In the exo-selective cyclization of mupirocin methyl ester.
• In the kinetic resolution of cyclic aliphatic syn-1,3-diols, which are used as valuable building blocks.

Reactions

1. Chiral phosphoric acid catalyst used for the highly enantioselective Friedel-Crafts reaction of indoles with imines.
2. Chiral phosphoric acid catalyst used for the highly enantioselective Friedel-Crafts reaction of pyrrole derivatives with N-acyl imines.
3. Chiral phosphoric acid catalyst used for the enantioselective transfer hydrogenation of hydroxylactams providing enantioenriched tetrahydro-β-carbolines (in dioxane) at room temperature (up to 94% yield, 90% ee).
4. [Rh2(OAc)4]/chiral phosphoric acid catalyst used for the enantioselective symmetric, three-component reaction of diazo compounds with imines and water yielding β-amino-α-hydroxy acid derivatives.
5. Enantioselective desymmetrization of prochiral allenic diols via cooperative catalysis of Pd(OAc)2 and a chiral phosphoric acid.