Tetrahydropyridines via FeCl3-Catalyzed Carbonyl–Olefin Metathesis

• DOI: 10.1021/acs.orglett.0c00918
• Publication Date: 2020-03-23T18:29:26Z
• Authors: Katie A. Rykaczewski; Emilia J. Groso; Hannah L. Vonesh; Mario A. Gaviria; Alistair D. Richa...; Troy E. Zehnder; Corinna S. Schindler
• Keywords: Pyrrolidines; Chlorides; Molecular Structure; Alkenes; Ferric Compounds; 01 natural sciences; Catalysis; 0104 chemical sciences

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.