Organic Letters
Organic Letters
5 years ago

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

Factors Governing and Application of the Cope Rearrangement of 3,3-Dicyano-1,5-dienes and Related Studies
Ehsan Fereyduni, Alexander J. Grenning
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01951

DOI: 10.1021/acs.orglett.7b01951

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