Issue 12, 2021

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
27 Feb 2021
Accepted
03 Apr 2021
First published
08 Apr 2021

Org. Chem. Front., 2021,8, 3069-3075

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

S. Li, Q. Qin, Z. Qi, L. Yang, Y. Kang, X. Zhang, A. Ma and J. Peng, Org. Chem. Front., 2021, 8, 3069 DOI: 10.1039/D1QO00303H

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