The Cope rearrangement of 3,3-dicyano-1,5-dienes is an over-looked, but attractive reaction for preparing useful building blocks for application in bioactive molecule synthesis. The substrates are derived from abundant chemical feedstocks, ketones/aldehydes, malonic acids, and allylic electrophiles, which thermally rearrange to γ-allyl alkylidenemalononitriles, bifunctional building blocks of high value to bioactive molecule synthesis. For example, we have shown in published and unpublished work that such building blocks can rapidly be converted to cycloheptene-, amide-containing-, and carbinol-containing scaffolds efficiently. For these reasons, we believe these substrates are of high value to bioactive, complex molecule synthesis. We have identified two main challenges that are limiting the value of the original Cope rearrangement in synthesis: (1) there are many substitution patterns (R1 – R3) that prevent a thermodynamically favorable Cope rearrangement. (2) How are the building blocks prepared enantioenriched? Presented at the ACS Meeting in San Diego will be our work aimed at addressing these current limitations.

Advancing the original cope rearrangement: Fundemental studies and applications in complex molecule synthesis

2019 Fall National Meeting

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