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. 2016 Jun 30;72(26):3759-3765.
doi: 10.1016/j.tet.2016.02.028. Epub 2016 Feb 18.

An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates

Michael L Conner  1 , M Kevin Brown  1
Affiliations

An unexpected Lewis acid catalyzed Diels-Alder cycloaddition of aryl allenes and acrylates

Michael L Conner et al. Tetrahedron. .

Abstract

An unexpected [4+2] cycloaddition of aryl allenes and simple acrylate derivatives is reported. This process functions well with a variety of allenes and acrylates to generate bi- and tricyclic dihydronaphthalene derivatives through a nonconventional bond disconnection.

Keywords: Acrylates; Allenes; Cycloaddition; Diels-Alder; Lewis-acid.

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Figures

Scheme 1
Scheme 1
Allene-based cycloadditions.
Scheme 2
Scheme 2
Relevant literature precedent.
Scheme 3
Scheme 3
Substrate scope.
Scheme 4
Scheme 4
Mechanistic investigations.
Scheme 5
Scheme 5
Proposed mechanism and transition state.
Scheme 6
Scheme 6
Chirality transfer reactions.
Chart 1
Chart 1
Limitations of method.
See this image and copyright information in PMC

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