Synthesis of γ,δ-Unsaturated α-Aminoaldehydes Using a Copper-Catalyzed Vinylation Reaction Followed by a Claisen Rearrangement

被引：11

作者：

Ricard, Simon ^{[1
]}

Sanapo, Gabriel F. ^{[1
]}

Rahem, Neel ^{[1
]}

Daoust, Benoit ^{[1
]}

机构：

[1] Univ Quebec Trois Rivieres, Dept Chim Biochim & Phys, Trois Rivieres, PQ G9A 5H7, Canada

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 12期

基金：

加拿大自然科学与工程研究理事会;

关键词：

N BOND FORMATION; C-O BOND; CROSS-COUPLING REACTIONS; DIARYL ETHERS; ARYL HALIDES; CUPRIC ACETATE; AMINO-ACIDS; AMIDES; CARBON; ROUTE;

D O I：

10.1021/acs.joc.6b00512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method to synthesize gamma,delta-unsaturated alpha-nitrogenated aldehydes in very good yields is described herein. This method involves a copper-coupling reaction between beta-iodoenamide derivatives and allylic alcohols to generate beta-allyloxyenamide derivatives. The latter, when heated, undergo a Claisen rearrangement and form gamma,delta-unsaturated alpha-nitrogenated aldehydes.

引用

页码：5066 / 5073

页数：8

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