TY - JOUR
T1 - Pd-Catalyzed Asymmetric Allylation Reaction of 2-Aryl-3H-indol-3-ones with Allyltrimethylsilane
AU - Yang, Fan
AU - Wang, Lun
AU - Liang, Meiqi
AU - Zhang, Linchun
AU - Fan, Baomin
AU - Yao, Bo
N1 - Publisher Copyright:
© 2024 American Chemical Society.
PY - 2024/2/2
Y1 - 2024/2/2
N2 - An efficient method for the first ene-reaction of 2-aryl-3H-indol-3-ones with allyltrimethylsilane has been developed for the first time. The reaction proceeded under the catalysis of Pd(OAc)2 and chiral phosphoric ligand L11 in the presence of Cu(CF3COO)2·XH2O, PivOH, and 5 Å molecular sieves in DMSO at 60 °C. The present methodology can avoid the impact of amine products generated by the reaction on the catalyst, and at the same time, the high catalytic activity of classical palladium catalysts still has catalytic ability for low electrophilic keto-imines. The desired products were furnished in excellent yields with good enantioselectivity.
AB - An efficient method for the first ene-reaction of 2-aryl-3H-indol-3-ones with allyltrimethylsilane has been developed for the first time. The reaction proceeded under the catalysis of Pd(OAc)2 and chiral phosphoric ligand L11 in the presence of Cu(CF3COO)2·XH2O, PivOH, and 5 Å molecular sieves in DMSO at 60 °C. The present methodology can avoid the impact of amine products generated by the reaction on the catalyst, and at the same time, the high catalytic activity of classical palladium catalysts still has catalytic ability for low electrophilic keto-imines. The desired products were furnished in excellent yields with good enantioselectivity.
UR - http://www.scopus.com/inward/record.url?scp=85183111076&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.3c02599
DO - 10.1021/acs.joc.3c02599
M3 - Article
AN - SCOPUS:85183111076
SN - 0022-3263
VL - 89
SP - 1873
EP - 1879
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 3
ER -