Organocatalyzed Enantioselective Amination for Quaternized Serines as Tertiary Amides.

Herein, we describe a -aminocatalyzed enantioselective α-hydrazination of an α-formyl amide for the production of protected quaternized serines as tertiary amides with 's of generally >98% and ≤99% yields. The proposed TS model supported by density functional theory calculations involves a quinuclidinium ion Brønsted acid-assisted delivery of DBAD, which occurs from the face of an H-bonded enaminone when using a 9-cinchonamine catalyst, resulting in a hydrazide with the -configuration as determined by X-ray analysis.