Nucleophilic α-Arylation and α-Alkylation of Ketones by Polarity Inversion of N-Alkoxyenamines: Entry to the Umpolung Reaction at the α-Carbon Position of Carbonyl Compounds

被引：84

作者：

Miyoshi, Tetsuya ^{[1
]}

Miyakawa, Takayuki ^{[1
]}

Ueda, Masafumi ^{[1
]}

Miyata, Okiko ^{[1
]}

机构：

[1] Kobe Pharmaceut Univ, Higashinada Ku, Kobe, Hyogo 6588558, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2011年 / 50卷 / 04期

基金：

日本学术振兴会;

关键词：

aluminum; enamines; ketones; nucleophilic addition; umpolung; TRIMETHYLENE DITHIOACETAL DERIVATIVES; COUPLING REACTIONS; GRIGNARD-REAGENTS; CROSS-COUPLINGS; GENERAL-METHOD; PALLADIUM; HALIDES; ALDEHYDES; ENAMINES; ESTERS;

D O I：

10.1002/anie.201004374

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new aspect of enamine chemistry: The formation of N-alkoxyenamines from ketones has led to an efficient umpolung reaction. The alkylation of N-alkoxyenamines with trialkylaluminum compounds proceeded smoothly and gave α-alkylated ketones (see scheme). This reaction offers a simple transformation of ketones into α-substituted ketones without the need to isolate enamines and intermediary imines. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：928 / 931

页数：4

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