Institute of Organic Chemistry, Chemistry Department, Lodz University of Technology , Żeromskiego 116, 90-924 Łódź, Poland.
J Org Chem. 2016 Aug 5;81(15):6800-7. doi: 10.1021/acs.joc.6b00975. Epub 2016 Jul 11.
A new strategy for the highly enantio- and diastereoselective synthesis of 3,4-dihydrocoumarin derivatives bearing a fused pyrrolidine ring is reported. It is based on a Brønsted base catalyzed cascade reactivity between β,γ-unsaturated-α-ketophosphonates and imines (derived from various salicylaldehydes and diethyl aminomalonate). The approach can be described as a doubly annulative strategy where both the pyrrolidine moiety and the δ-lactone ring of the 3,4-dihydrocoumarin framework are constructed starting from acyclic precursors.
本文报道了一种新型的高对映选择性和非对映选择性合成具有稠合吡咯烷环的 3,4-二氢香豆素衍生物的策略。该策略基于 Brønsted 碱催化的β,γ-不饱和-α-酮膦酸酯和亚胺（由各种水杨醛和二乙氨基丙二酸酯衍生而来）之间的级联反应。该方法可以描述为一种双重环合策略，其中吡咯烷部分和 3,4-二氢香豆素骨架的δ-内酯环都是从非环前体构建而成的。
