Regioselective Addition of Quinoline Derivatives to Carbonyl Compounds via Palladium-Catalyzed Umpolung with Diethylzinc

被引：3

作者：

Matsumoto, Yohei ^{[1
]}

Yamamoto, Kosuke ^{[1
]}

Kuriyama, Masami ^{[1
]}

Nishida, Koyo ^{[1
]}

Onomura, Osamu ^{[1
]}

机构：

[1] Nagasaki Univ, Grad Sch Biomed Sci, 1-14 Bunkyo Machi, Nagasaki 8528521, Japan

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 08期

关键词：

palladium catalysis; diethylzinc; Umpolung; dihydroquinoline; regioselectivity; C-H FUNCTIONALIZATION; PI-ALLYLPALLADIUM; ENANTIOSELECTIVE ADDITION; ALLYLIC ACETATES; CHROMENE ACETALS; ALLYLATION; METAL; ALDEHYDES; NICKEL; ALKYLATION;

D O I：

10.1055/s-0037-1610682

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the C-4-selective addition of quinoline derivatives to carbonyl compounds is described. The combination of 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinolines (EEDQs) with a palladium catalyst and diethylzinc generates nucleophilic allyl species which undergo addition to various aldehydes and ketones. C-4-Substituted quinoline derivatives are obtained in high to excellent yields with moderate diastereoselectivities.

引用

页码：1795 / 1802

页数：8

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