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

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 t...

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Veröffentlicht in:Organic Chemistry Frontiers 2020-09, Vol.7 (18), p.2682-2688
Hauptverfasser: Li, Tong, Yan, Dandan, Cui, Chaoxing, Song, Xixi, Chang, Junbiao
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Sprache:eng
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Zusammenfassung: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%.
ISSN:2052-4129
2052-4110
2052-4129
2052-4110
DOI:10.1039/D0QO00770F