Synthesis of β,γ-unsaturated ketones with quaternary centers through regioselective hydroacylation of allenes with acyl chlorides

被引：6

作者：

Yoon, Subin ^{[1
]}

Lee, Kyeongmin ^{[1
]}

Kamranifard, Telma ^{[1
]}

Lee, Yunmi ^{[1
]}

机构：

[1] Kwangwoon Univ, Dept Chem, Seoul 01897, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2022年 / 43卷 / 12期

基金：

新加坡国家研究基金会;

关键词：

all-carbon quaternary centers; allenes; copper catalysis; hydroacylation; beta; gamma-unsaturated ketones; CATALYZED HYDROACYLATION; C-C; COPPER; FUNCTIONALIZATION; TRANSFORMATIONS; STEREOCENTERS; ALLYLATION; ALKENES; DIENES;

D O I：

10.1002/bkcs.12629

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The one-pot synthesis of beta,gamma-unsaturated ketones bearing all-carbon quaternary centers at the alpha-position via a highly regioselective hydroacylation of allenes using acyl chlorides and aluminum hydride is reported. The Cu-catalyzed hydroalumination of 1,1-disubstituted and 1,1,3-trisubstituted allenes with diisobutylaluminum hydride resulted in allylaluminum reagents that underwent regioselective acylation in the presence of acid chlorides. Various derivatives of allenes and acyl chlorides were compatible with this process, and alpha-quaternary ketones were obtained in high yields with excellent regioselectivity.

引用

收藏

页码：1307 / 1311

页数：5

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