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Hydroxy-Directed Ruthenium-Catalyzed Alkene/Alkyne Coupling: Increased Scope, Stereochemical Implications, and Mechanistic Rationale

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Rummelt,  Stephan M.
Research Department Fürstner, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Cheng,  Gui-Juan
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Gupta,  Puneet
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Thiel,  Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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

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Citation

Rummelt, S. M., Cheng, G.-J., Gupta, P., Thiel, W., & Fürstner, A. (2017). Hydroxy-Directed Ruthenium-Catalyzed Alkene/Alkyne Coupling: Increased Scope, Stereochemical Implications, and Mechanistic Rationale. Angewandte Chemie International Edition, 56(13), 3599-3604. doi:10.1002/anie.201700342.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002C-DB7F-A
Abstract
The recognition of the dual binding mode of propargyl and allyl alcohols to [Cp*Ru] fragments fostered the development of a highly regioselective intermolecular Alder-ene-type reaction of alkynes with 1,2-disubstituted alkenes. The increased substrate scope opens new perspectives in stereochemical terms. As the loaded catalyst is chiral-at-metal, stereochemical information is efficiently relayed from the propargylic site to the emerging C−C bond. This interpretation is based on the X-ray structure of the first Cp*Ru complex carrying an intact enyne ligand, and provides valuable insights into bonding and activation of the substrates. Computational data draw a clear picture of the principles governing regio- and stereocontrol.