Factors Governing and Application of the Cope Rearrangement of 3,3-Dicyano-1,5-dienes and Related Studies

Ehsan Fereyduni, Alexander J. Grenning

Research output: Contribution to journalArticlepeer-review

11 Scopus citations

Abstract

Cope and co-workers reported the [3,3] rearrangement of 3,3-dicyano-1,5-dienes in the early 1940s ("The Cope rearrangement"). However, these original substrates have remained largely unstudied until recently. Herein we explore styrene-deconjugating Cope rearrangements, a diastereoselective Cope rearrangement/deconjugative α-allylation sequence, and factors governing α- vs γ-allylation regioselectivity of Knoevenagel adduct allyl anions. Ultimately, these studies result in the synthesis of diverse and functionally dense polycycloalkane frameworks from abundant reagents using simple chemistry.

Original languageEnglish (US)
Pages (from-to)4130-4133
Number of pages4
JournalOrganic Letters
Volume19
Issue number15
DOIs
StatePublished - Aug 4 2017
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2017 American Chemical Society.

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