Cobalt-Catalyzed Intramolecular [4 + 2] Cycloaddition of Cyclopropyl-Capped Dienes with Alkynes/Alkenes/Allene and Reaction Mechanism.

Org Lett

Beijing National Laboratory for Molecular Sciences (BNLMS), Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry, Peking University, Beijing 100871, China.

Published: December 2024

A cobalt-catalyzed intramolecular [4 + 2] cycloaddition of cyclopropyl (CP)-capped dienes with ynes/enes/allene was reported, providing an efficient method toward a spiro[2.5]octene ring system found in natural products, such as illudin. The [4 + 2] cycloadducts can be converted into other compounds via CP chemistry. This reaction can also be catalyzed by Ni. A density functional theory study on the reaction mechanisms is also reported here.

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http://dx.doi.org/10.1021/acs.orglett.4c03772DOI Listing

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