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Updated: Dec 25, 2025

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis
Katie A Rykaczewski1, Emilia J Groso1, Hannah L Vonesh1
1Department of Chemistry, Willard Henry Dow Laboratory, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, United States.
Abstract:
Herein we describe the application of Lewis-acid-catalyzed carbonyl-olefin metathesis toward the synthesis of 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.
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