73582-32-8Relevant academic research and scientific papers
Asymmetric conjugate 1,4-addition of arylboronic acids to α,β-unsaturated esters catalyzed by rhodium(I)/(S)-binap
Sakuma, Satoshi,Sakai, Masaaki,Itooka, Ryoh,Miyaura, Noria
, p. 5951 - 5955 (2000)
Arylboronic acids underwent the conjugate 1,4-addition to α,β-unsaturated esters to give β-aryl esters in high yields in the presence of a rhodium(I) catalyst. The addition of arylboronic acids to isopropyl crotonate resulted in high yields and high enantioselectivity exceeding 90% ee in the presence of 3 mol % of Rh(acac)(C2H4)2 and (S)-binap at 100 °C. The rhodium/(S)-binap complex provided (R)-3-phenylbutanoate in the addition of phenylboronic acid to benzyl crotonate. The effects on the enantioselectivity of chiral phosphine ligands, rhodium precursors, and substituents on α,β-unsaturated esters are discussed, as well as the mechanistic aspect of the catalytic cycle.
