Accessing the decarboxylative allylation–divinylcyclopropane-cycloheptadiene rearrangement from the ketone/aldehyde substrate pool

Richard Schroeder, Alexander J. Grenning

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

Herein reported is access to allyl γ-butyrolactones and caprolactones that can undergo decarboxylative allylation/divinylcyclopropane–cycloheptadiene rearrangement. The overall sequence is brief (5 steps from commercial ketones/aldehydes) and yields diverse cycloheptadienes. The key decarboxylative allylation/divinylcyclopropane–cycloheptadiene rearrangement was unknown at the outset of our studies but recently reported by the Nemoto group. We disclose a complementary study to Nemoto's that further demonstrates the value of this transformation. Specifically, new routes to the key substrates are disclosed that ultimately results in improved scope of target cycloheptadienes.

Original languageEnglish (US)
Pages (from-to)3231-3238
Number of pages8
JournalTetrahedron
Volume75
Issue number24
DOIs
StatePublished - Jun 14 2019
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2019

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