(S)-BINOL

(S)-BINOL

Chiral Catalysts, Ligands, Reagents, Privileged Ligands and Complexes, Asymmetric Synthesis, Chemical Synthesis, and BINOL's

(S)-BINOL is a versatile reagent having several applications:

1) (S)-BINOLforms a S-(-)-BINOL-Ti complex in combination with titanium(IV) isopropoxide which is an efficient chiral catalyst for (a) asymmetric addition of alkynylzinc to unactivated ketones (Ref: European Journal of Organic Chemistry 2006(5), 1303-1309, (2006)); (b) enantioselective ring-opening reaction of meso-stilbene oxide and cyclohexene oxide with anilines (Ref: Angewandte Chemie (Weinheim an der Bergstrasse, Germany) 119(28), 5469-5472, (2007)); and (c) asymmetric aryl transfers from triaryl(tetrahydrofuran)aluminum reagents to a wide variety of ketones (Ref: Tetrahedron Letters 36(43), 7897-7900, (1995))

2) (S)-BINOL is a phosphoramidite catalyst precursor that can be used to convert allylic alcohols to allylic amines

Ref: Angewandte Chemie (International ed. in English), 46(17), 3139-3143 (2007-3-14)

3) (S)-BINOL reacts with zirconium(IV) isopropoxide to form a chiral Lewis acid complex that can enable facile enantioselective allylation of aldehydes by allyltributyltin

Ref: Tetrahedron Letters 36(43), 7897-7900, (1995)

4) (S)-BINOL is a precursor for several industrially important ligands (S-BINAP)

Ref: Ref: Chem. Rev. 2005, 105, 3, 857–898