Synthesis of γ,γ-Disubstituted Butenolides through a Doubly Vinylogous Organocatalytic Cycloaddition
作者:Anna Skrzyńska、Piotr Drelich、Sebastian Frankowski、Łukasz Albrecht
DOI:10.1002/chem.201804650
日期:2018.11.7
organocatalytic approach to γ,γ‐disubstituted butenolides is described. It is based on a fully site‐selective functionalization of 5‐alkylidenefuran‐2(5H)‐ones via trienamine‐mediated [4+2]‐cycloaddition with α,β,γ,δ‐diunsaturated aldehydes. The developed methodology proceeds with excellent stereocontrol and constitutes a unique example of trienamine chemistry with vinylogous dienophiles. Importantly,
描述了一种新颖的有机催化方法,用于γ,γ-二取代的丁烯内酯。它基于通过三烯胺介导的[4 + 2]-环加成与α,β,γ,δ-二不饱和醛对5-亚烷基呋喃-2(5 H)-进行全位选择性官能化的基础。所开发的方法具有出色的立体控制能力,并构成了乙烯基烯二亲物的三烯胺化学的独特实例。重要的是,该反应的范围非常广泛,并允许在丁烯内酯环的α-或β-位置也引入取代基。在导致多环产物的分子内Stetter反应中已经证实了所获得的产物的有用性。