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Chiral Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis

preprint
submitted on 21.10.2019 and posted on 23.10.2019 by Katie Rykaczewski, Emilia J. Groso, Hannah L. Vonesh, Mario Gaviria, Alistair D. Richardson, Troy E. Zehnder, Corinna Schindler

Herein, we describe the application of Lewis acid-catalyzed carbonyl-olefin metathesis towards the synthesis of chiral, substituted tetrahydropyridines from commercially available amino acids as chiral pool reagents. This strategy relies on FeCl3 as an inexpensive and environmentally benign catalyst and enables access to a variety of substituted tetrahydropyridines under mild reaction conditions. The reaction proceeds with complete stereoretention and is viable for a variety of natural and unnatural amino acids to provide the corresponding tetrahydropyridines in up to 99% yield.


Funding

NIGMS R01-GM118644

Alfred P. Sloan Foundation

Camille and Henry Dreyfus Foundation

David and Lucile Packard Foundation

History

Email Address of Submitting Author

corinnas@umich.edu

Institution

University of Michigan

Country

United States

ORCID For Submitting Author

0000-0003-4968-8013

Declaration of Conflict of Interest

no conflict of interest

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