Zn(II)-Catalyzed Asymmetric Transfer Hydrogenation of γ-Indolyl β,γ-Unsaturated α-Keto Amides and α-Keto Esters with Hantzsch Ester

被引:0
作者
Zhang, Xing-Ping [1 ]
Lian, Sai-Ya [1 ]
Wang, Hai-Xia [1 ]
Xie, Ming-Sheng [1 ]
Guo, Hai-Ming [1 ]
机构
[1] Henan Normal Univ, Sch Chem & Chem Engn, State Key Lab Antiviral Drugs, Key Lab Green Chem Media & React,Minist Educ,Pingy, Xinxiang 453007, Henan, Peoples R China
关键词
asymmetric catalysis; transfer hydrogenation; hantzsch ester; lewis acids; ENANTIOSELECTIVE TRANSFER HYDROGENATION; 3+2 CYCLOADDITION; IMINO ESTERS; LEWIS-ACID; KETOESTERS; REDUCTION; LIGANDS; CECL3-CENTER-DOT-7H(2)O;
D O I
10.1002/adsc.202500158
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Highly enantioselective transfer hydrogenation of gamma-indolyl beta,gamma-unsaturated alpha-keto amides and alpha-keto esters with Hantzsch ester catalyzed by chiral zinc complex is reported. Using 5 mol% of Zn(OTf)2-imidazolidine-pyrroloimidazolone pyridine as the catalyst, the C=C bond in gamma-indolyl beta,gamma-unsaturated alpha-keto amides is selectively reduced, affording hydrogenation products in high yields (up to 99% yield) and excellent enantioselectivities (up to 99% ee). Using the same catalyst system, the C=O bond in alpha-keto esters is reduced, generating alpha-hydroxy esters in good results (up to 99% yield and 98% ee). A retro-Michael pathway and subsequent transfer hydrogenation reaction are proposed for the explanation of the side products in the transfer hydrogenation of gamma-indolyl beta,gamma-unsaturated alpha-keto amides.
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页数:8
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