ANIPE-Cu Catalyst Enables Highly Enantioselective Markovnikov Hydroboration of α-Olefins

Asymmetric hydroboration of simple and unactivated terminal alkenes (α-olefins), feedstock chemicals derived from the petrochemical industry, has not been efficiently realized for past decades. Using a bulky ANIPE ligand, we achieved a rare example of highly enantioselective copper-catalyzed Markovnikov hydroboration of α-olefins. The chiral secondary alkylboronic ester products were obtained in moderate to good yields and regioselectivities with excellent enantioselectivities.1 Introduction2 Conditions Optimization3 Substrate Scope4 Application5 Mechanistic Discussion6 Conclusions and Future Directions

ANIPE-Cu Catalyst Enables Highly Enantioselective Markovnikov Hydroboration of α-Olefins

Asymmetric hydroboration of simple and unactivated terminal alkenes (α-olefins), feedstock chemicals derived from the petrochemical industry, has not been efficiently realized for past decades. Using a bulky ANIPE ligand, we achieved a rare example of highly enantioselective copper-catalyzed Markovnikov hydroboration of α-olefins. The chiral secondary alkylboronic ester products were obtained in moderate to good yields and regioselectivities with excellent enantioselectivities.1 Introduction2 Conditions Optimization3 Substrate Scope4 Application5 Mechanistic Discussion6 Conclusions and Future Directions

Facile access to functionalized chiral secondary benzylic boronic esters via catalytic asymmetric hydroboration

Allylic and homoallylic phosphonates undergo asymmetric hydroboration yielding chiral boronic esters (yields up to 86%, enantiomer ratios up to 99 : 1).