1198356-01-2

Upstream product

• 55282-95-6 ethyl (2E)-5-phenylpent-2-enoate 
• 73183-34-3 bis(pinacol)diborane 
• 88842-13-1 (Z-)-ethyl 5-phenylpent-2-enoate 

Downstream Products

• 182417-58-9 (R)-3-hydroxy-5-phenyl-pentanoic acid ethyl ester 

Relevant academic research and scientific papers

Asymmetric β-boration of α,β-unsaturated carbonyl compounds with chiral Rh[bis(oxazolinyl)phenyl] catalysts

Chiral rhodium[bis(oxazolinyl)phenyl] complexes exhibited high catalytic activity for the β-boration of α,β-unsaturated esters, ketones, and amides with bis(pinacolato)diboron in the presence of sodium tert-butoxide to attain high enantioselectivity of up to 97%. The substrate scope and catalytic mechanism were discussed.

Copper-catalyzed boration of activated alkynes. Chiral boranes via a one-pot copper-catalyzed boration and reduction protocol

Phosphine-copper(I) complexes efficiently catalyzed the mono-boration of electron-deficient alkynes in the presence of MeOH and also catalyzed conjugate reductions of alkenylboronates bearing an electron-withdrawing group. The mono-addition of bis(pinacolato)diboron to alkynes catalyzed by a copper-Xantphos complex produced vinylboronates with high regio and stereoselectivity and asymmetric reduction of the vinylboronates by a chiral copper-bisphosphine catalyst allowed the synthesis of valuable chiral boranes with high enantioselectivity. One-pot boration/asymmetric reduction of α,β-unsaturated alkynoates could be conducted with a single copper-phosphine catalyst.

Asymmetric β-boration of α,β-unsaturated carbonyl compounds promoted by chiral rhodium-bisoxazolinylphenyl catalysts

Chiral rhodium-bisoxazolinylphenyl acetate complexes exhibited high catalytic activity for the β-boration of α,β-unsaturated carbonyl compounds with bis(pinacolato)diboron in the presence of sodium t-butoxide with enantioselectivity up to 97%.

Catalytic asymmetric boration of acyclic α,β-unsaturated esters and nitriles

(Chemical Equation Presented) Asymmetrie β-boration of acyclic α,β-unsaturated carbonyl compounds provides ready access to enantioenriched functionalized organoboron compounds. A range of acyclic unsaturated esters and nitriles reacted with high enantioselectivity and good yields at room temperature using a copper catalyst and planar chiral diphosphine ligands (L).