铑催化喹唑啉酮与丙二烯及烯丙基碳酸酯的不对称N-H官能化反应：（-）-Chaetominine的首次对映选择性形式全合成
Rhodium-Catalyzed Asymmetric N-H Functionalization of Quinazolinones with Allenes and Allylic Carbonates: The First Enantioselective Formal Total Synthesis of (-)-Chaetominine.
作者信息
Zhou Yirong, Breit Bernhard
机构信息
Institut für Organische Chemie and Freiburg Institute of Advanced Studies (FRIAS), Albert-Ludwigs-Universität, Alberstr. 21, 79104, Freiburg, Germany.
Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, China.
出版信息
Chemistry. 2017 Dec 22;23(72):18156-18160. doi: 10.1002/chem.201705059. Epub 2017 Dec 5.
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.
在手性双齿二膦配体的协助下，通过铑催化成功实现了喹唑啉酮与丙二烯和烯丙基碳酸酯前所未有的不对称N-H官能化。该方法的高效性和实用性体现在1 mol %的低催化剂负载量以及具有广泛官能团兼容性的出色化学、区域和对映选择性上。此外，这一最新开发的策略被应用于（-）-chaetominine的首次对映选择性形式全合成的关键步骤中。
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