Synthesis of disubstituted γ-butyrolactones and spirocyclopropanes via a multicomponent reaction of aldehydes, Meldrum's acid and sulfoxonium ylides†
Shan-Shan Li,Qi Qin,Zhuang Qi,Li-Miao Yang,Yun Kang,Xiang-Zhi Zhang,Ai-Jun Ma,Jin-Bao Peng
Organic Chemistry Frontiers Pub Date : 04/08/2021 00:00:00 , DOI:10.1039/D1QO00303H
Abstract

An efficient synthesis of disubstituted γ-butyrolactones and spirocyclopropanes via a multicomponent reaction of aldehydes, Meldrum's acid and sulfoxonium ylides has been developed. Under mild conditions, electron-rich aromatic aldehydes reacted with Meldrum's acid and sulfoxonium ylides and produced trans-β,γ-disubstituted γ-butyrolactones, while neutral and electron-deficient aromatic aldehydes and aliphatic aldehydes led to the formation of trans-spirocyclopropanes. The cyclopropane could be converted to the γ-butyrolactone under Lewis acid conditions.

Graphical abstract: Synthesis of disubstituted γ-butyrolactones and spirocyclopropanes via a multicomponent reaction of aldehydes, Meldrum's acid and sulfoxonium ylides