Derivatives of Alkyl 2-Hydroxy-3-oxocyclopent-1-enecarboxylates and Intermolecular [4+2] Cycloadditions of Cyclopentadienones Prepared TherefromThis work was supported by the National Science Foundation (CHE-0910208) to whom we are grateful.
Received: 04 May 2018
Accepted: 18 May 2018
05 July 2018 (eFirst)
Published as part of the Special Section dedicated to Scott E. Denmark on the occasion of his 65th birthday.
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 wordscycloaddition - cyclopentadienones - Diels–Alder reaction - carbocycles - phosphorylation - reactive intermediates
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