Rhodium-Catalyzed Asymmetric N-H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (-)-Chaetominine

被引：28
|
作者：
Zhou, Yirong [1 ,2 ,3 ]
Breit, Bernhard [1 ,2 ]
机构：
[1] Albert Ludwigs Univ, Inst Organ Chem, Alberstr 21, D-79104 Freiburg, Germany
[2] Albert Ludwigs Univ, Freiburg Inst Adv Studies FRIAS, Alberstr 21, D-79104 Freiburg, Germany
[3] Jiangxi Normal Univ, Coll Chem & Chem Engn, Minist Educ, Key Lab Funct Small Organ Mol, Nanchang 330022, Jiangxi, Peoples R China
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2017年 / 23卷 / 72期
基金：
中国国家自然科学基金;
关键词：
allenes; asymmetric allylation; chaetominines; quinazolinones; rhodium; TERMINAL ALLENES; REGIO; ALLYLATION; AMINATION; HETEROCYCLES; SUBSTITUTION; PALLADIUM; INDOLES; CHAETOMININE; CHEMISTRY;
D O I：
10.1002/chem.201705059
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An unprecedented asymmetric N-H functionalization of quinazolinones with allenes and allylic carbonates was successfully achieved by rhodium catalysis with the assistance of chiral bidentate diphosphine ligands. The high efficiency and practicality of this method was demonstrated by a low catalyst loading of 1 mol% as well as excellent chemo-, regio-, and enantioselectivities with broad functional group compatibility. Furthermore, this newly developed strategy was applied as key step in the first enantioselective formal total synthesis of (-)-chaetominine.
引用
收藏
页码：18156 / 18160
页数：5
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