Issue 18, 2020

A thermal decarboxylative Cloke–Wilson rearrangement of dispirocyclopropanes derived from para-quinone methides and bromo-Meldrum's acids: an approach to synthesize spirobutyrolactone para-dienones

Abstract

An unprecedented approach to synthesize spirobutyrolactone para-dienones from para-quinone methides and bromo-Meldrum's acids has been developed. A series of spatially congested dispirocyclopropanes are generated by spirocyclopropanation, and their unique reactivities have been explored for the first time in the thermal decarboxylative Cloke–Wilson rearrangement reaction. A variety of spirobutyrolactones are efficiently produced via the sequential spirocyclopropanation/rearrangement process in two steps with overall yields from 56 to 88%.

Graphical abstract: A thermal decarboxylative Cloke–Wilson rearrangement of dispirocyclopropanes derived from para-quinone methides and bromo-Meldrum's acids: an approach to synthesize spirobutyrolactone para-dienones

Supplementary files

Article information

Article type
Research Article
Submitted
28 Jun 2020
Accepted
08 Aug 2020
First published
11 Aug 2020

Org. Chem. Front., 2020,7, 2682-2688

A thermal decarboxylative Cloke–Wilson rearrangement of dispirocyclopropanes derived from para-quinone methides and bromo-Meldrum's acids: an approach to synthesize spirobutyrolactone para-dienones

T. Li, D. Yan, C. Cui, X. Song and J. Chang, Org. Chem. Front., 2020, 7, 2682 DOI: 10.1039/D0QO00770F

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