Asymmetric Synthesis of Small Molecule Inhibitors of IL-17A via Crystallization-Induced Diastereoselective Strecker
Stephen N Greszler1, Gang Zhao1, Michael A Leitch2
1Research & Development, AbbVie, Inc., 1 N Waukegan Rd, North Chicago, Illinois 60064, United States.
Abstract:
Crystallization-induced asymmetric transformations can dramatically alter the product ratio from a reaction with inherently poor or undesired selectivity. Reported herein is a rare example of a dynamic crystallization-induced diastereoselective Strecker reaction which overrides the inherent substrate bias in the preparation of aryl-substituted tetrahydrofuran-derived non-natural amino acids. Discovery of a new non-hydrogenative auxiliary cleavage method enables application of the Strecker reaction to the large-scale syntheses of small molecule inhibitors of IL-17A.
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