(R)-Tol-BINAP

Application

(R)-Tol-BINAP, a white to cream powder, serves as a versatile chiral catalyst ligand with a wide range of applications in asymmetric synthesis. As a complex derived from rhodium precursors, (R)-Tol-BINAP is utilized for the asymmetric hydroformylation of vinyl acetate and plays a crucial role in the reductive amination of ketones. It also functions as a ligand for Pt dications in cation trapping and supports Rh(I)-catalyzed hydrogenation of acetamidoacrylic acid derivatives. This chiral catalyst can be applied to the allylation of N-tosyl α-imino esters and is an effective ligand in palladium-catalyzed carbon-oxygen bond formation and α-arylation of ketones. Additionally, it serves as a ligand for copper-catalyzed asymmetric conjugate reduction, dienolate addition to aldehydes, and the enantioselective reduction of lactones and lactams. (R)-Tol-BINAP also aids in the enantioselective cycloaddition of allenylsilanes with α-imino esters and catalyzes the Aldol reaction to ketones. In rhodium catalysis, it facilitates the [2+2+2] cycloaddition reactions of alkenes and alkynes, and in copper catalysis, it is instrumental in asymmetric conjugate additions of alkyl Grignard reagents on α,β-unsaturated esters as well as in the synthesis of cyclopropanes through tandem conjugate addition and intramolecular enolate trapping. Furthermore, the p-Tol-BINAP·AgF complex has been reported to catalyze the asymmetric Mukaiyama-type aldol reaction, highlighting its functionality based on its bis-naphthalene backbone with diverse phosphine derivatives.