Asymmetric Synthesis of Oxa-Bridged Oxazocines through a Catalytic RhII/ZnII Relay [4+3] Cycloaddition Reaction

被引：47
|
作者：
Xu, Chaoran [1 ]
Wang, Kaixuan [1 ]
Li, Dawei [1 ]
Lin, Lili [1 ]
Feng, Xiaoming [1 ]
机构：
[1] Sichuan Univ, Coll Chem, Minist Educ, Key Lab Green Chem & Technol, Chengdu 610064, Sichuan, Peoples R China
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 51期
基金：
中国国家自然科学基金;
关键词：
asymmetric catalysis; diazo compounds; bimetallic catalysis; oxa-bridged oxazocines; relay catalysis; 1,3-DIPOLAR CYCLOADDITION; CYCLIZATION CYCLOADDITION; DUAL CATALYSIS; INTRAMOLECULAR CYCLOADDITION; ALLYLIC ALKYLATION; CARBONYL YLIDES; ALPHA; DERIVATIVES; CHEMISTRY; ISOMUNCHNONES;
D O I：
10.1002/anie.201910898
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Oxa-bridged oxazocines bearing three chiral carbon centers were synthesized efficiently through a bimetallic catalytic asymmetric tandem reaction of beta,gamma-unsaturated alpha-ketoesters with diazoimides. The process contained a rhodium-promoted in situ generation of isomunchnone from diazoimide decomposition, and a [4+3]-cycloaddition of beta,gamma-unsaturated alpha-ketoester catalyzed by a chiral N,N '-dioxide-Zn-II complex. Ligand-accelerated catalysis was found, and a possible transition-state model was proposed to explain the origin of stereoselectivity.
引用
收藏
页码：18438 / 18442
页数：5
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