Two Manifolds for Metal-Catalyzed Intramolecular Diels-Alder Reactions of 
Unactivated Alkynes

Fürstner, Alois; Stimson, Christopher C.

doi:10.1002/anie.200703321

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Two Manifolds for Metal-Catalyzed Intramolecular Diels-Alder Reactions of Unactivated Alkynes

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Fürstner, Alois
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Stimson, Christopher C.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Fürstner, A., & Stimson, C. C. (2007). Two Manifolds for Metal-Catalyzed Intramolecular Diels-Alder Reactions of Unactivated Alkynes. Angewandte Chemie International Edition, 46(46), 8845-8849. doi:10.1002/anie.200703321.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0025-AD1B-A

Abstract

Being unconventional: Although conventional metal-catalyzed [4+2] cycloadditions of inactivated dienynes are known to proceed by an oxidative cyclization/insertion mechanism, two entirely different pathways also result in formal Diels–Alder reactions (see scheme). These alternative mechanisms open new vistas for further functionalization of the products, as exemplified by an unprecedented cycloaddition/alkylation cascade.