Enantioselective N-heterocyclic carbene-catalyzed rearrangement of enol ε-lactones

被引：4
|
作者：
Qiu, Ye [1 ,2 ]
Liang, Zhi-Qin [1 ]
Chen, Kun-Quan [1 ]
Dai, Lei [1 ]
Ye, Song [1 ,2 ]
机构：
[1] Chinese Acad Sci, Inst Chem, CAS Res Educ Ctr Excellence Mol Sci, Beijing Natl Lab Mol Sci,CAS Key Lab Mol Recognit, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期
基金：
中国国家自然科学基金;
关键词：
SATURATED CARBOXYLIC ESTERS; DYNAMIC KINETIC RESOLUTION; ORGANOCATALYTIC ACTIVATION; ALDOL-LACTONIZATION; BETA-LACTONES; KETENES; ALPHA; CYCLOADDITION; ANNULATION; ACCESS;
D O I：
10.1039/d2qo01721k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
beta-Lactones are common substructures in bioactive molecules. Herein, we developed an enantioselective N-heterocyclic carbene (NHC)-catalyzed rearrangement of enol epsilon-lactones for the construction of bicyclic beta-lactones. The reaction works well for both exo- and endo-enol epsilon-lactones, giving the corresponding bicyclic beta-lactones with two or three contiguous stereocenters, respectively. The reaction features readily available starting materials, 100% atom economy, mild conditions, high diastereo- and enantioselectivity.
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页码：799 / 805
页数：7
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