期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 65, 期 19, 页码 5951-5955出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo0002184
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Arylboronic acids underwent the conjugate 1,4-addition to alpha,beta-unsaturated esters to give beta-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 degrees 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 alpha,beta-unsaturated esters are discussed, as well as the mechanistic aspect of the catalytic cycle.
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