Catalysis

Chiral Tetrahydropyridines via FeCl3-Catalyzed Carbonyl-Olefin Metathesis

Abstract

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.


Content

Thumbnail image of Manuscript October 21st.pdf

Supplementary material

Thumbnail image of Tetrahydropyridines October 2019.pdf
Tetrahydropyridines October 2019