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Synthesis 2018; 50(22): 4483-4489
DOI: 10.1055/s-0037-1610184
paper
© Georg Thieme Verlag Stuttgart · New York

Derivatives of Alkyl 2-Hydroxy-3-oxocyclopent-1-enecarboxylates and Intermolecular [4+2] Cycloadditions of Cyclopentadienones Prepared Therefrom

Aswin Garimalla
,
Michael Harmata*
This work was supported by the National Science Foundation (CHE-0910208) to whom we are grateful.
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Publication History

Received: 04 May 2018

Accepted: 18 May 2018

Publication Date:
05 July 2018 (online)

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Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday.

Abstract

Some derivatives of alkyl 2-hydroxy-3-oxocyclopent-1-enecarboxylates have been synthesized and their reactivity as progenitors of cyclopentadienones for intermolecular [4+2]-cycloaddition reactions has been evaluated. It was found that the derivative containing a phosphate ester leaving group gave better yields in the cycloaddition reaction among the derivatives studied. The yields of the cycloaddition reactions were moderate, perhaps due side reactions not leading to the reactive intermediate cyclopentadienone.

Key words

cycloaddition - cyclopentadienones - Diels–Alder reaction - carbocycles - phosphorylation - reactive intermediates

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610184.
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