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Synthesis of Cyclopentenols and Cyclopentenones via Nickel-Catalyzed Reductive Cycloaddition

Aireal D. Jenkins, Ananda Herath, Minsoo Song and John Montgomery*

*930 North University Avenue, Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109-1055, United States, Email:

A. D. Jenkins, A. Herath, M. Song, J. Montgomery, J. Am. Chem. Soc., 2011, 133, 14460-14466.

DOI: 10.1021/ja206722t

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A nickel-catalyzed enal-alkyne cycloaddition directly affords cyclopentenols, whereas an enoate-alkyne cycloaddition affords the analogous cyclopentenones. The mechanism of these processes likely involves formation and protonation of a metallacyclic intermediate. The general strategy provides a straightforward entry to five-membered ring products from simple, stable π-systems.

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ID: J48-Y2011-2620