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Synthesis 2018; 50(22): 4483-4489
DOI: 10.1055/s-0037-1610184
DOI: 10.1055/s-0037-1610184
paper
Derivatives of Alkyl 2-Hydroxy-3-oxocyclopent-1-enecarboxylates and Intermolecular [4+2] Cycloadditions of Cyclopentadienones Prepared Therefrom
This work was supported by the National Science Foundation (CHE-0910208) to whom we are grateful.Further Information
Publication History
Received: 04 May 2018
Accepted: 18 May 2018
Publication Date:
05 July 2018 (online)
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 intermediatesSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610184.
- Supporting Information
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