Kowalczyk-Dworak Dorota, Albrecht Łukasz
Institute of Organic Chemistry, Faculty of Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924 Łódź, Poland.
Org Biomol Chem. 2019 Mar 6;17(10):2624-2628. doi: 10.1039/c9ob00068b.
A new, organocatalytic doubly annulative cascade utilizing α,β-unsaturated butenolides and imines (derived from salicyl aldehydes and α-amino-γ-lactones) as starting materials is described. The developed strategy is based on two annulative processes: (1) initial [3 + 2]-dipolar cycloaddition allowing for the construction of a pyrrolidine ring; and (2) the butenolide-ring-opening reaction leading to the introduction of a 3,4-dihydrocoumarin framework. Target polycyclic compounds have been obtained with excellent chemical and stereochemical efficiencies.
描述了一种新的有机催化双环化串联反应，该反应以α,β-不饱和丁烯内酯和亚胺（由水杨醛和α-氨基-γ-内酯衍生而来）为起始原料。所开发的策略基于两个环化过程：（1）初始的[3 + 2]偶极环加成反应，用于构建吡咯烷环；（2）丁烯内酯开环反应，导致引入3,4-二氢香豆素骨架。已以优异的化学和立体化学效率获得了目标多环化合物。
