Enantioselective α-Amination of Amides by One-Pot Organo-/Iodine Sequential Catalysis

Org Lett. 2024 Jan 12;26(1):258-263. doi: 10.1021/acs.orglett.3c03925. Epub 2023 Dec 29.

Abstract

An one-pot organo- and iodine sequential catalysis strategy for reactions of amides with pyrazole-based primary amines was described to synthesize chiral α-amino amides with a quaternary stereocenter. This methodology exhibited strong asymmetric induction, resulting in a typical enantiomeric excess value exceeding 99% and diastereoselectivity up to >99:1 dr. Moreover, the reaction was conducted without the use of any metals or strong bases.