Chiral Metal Salts as Ligands for Catalytic Asymmetric Mannich Reactions with Simple Amides

J Am Chem Soc. 2021 Apr 21;143(15):5598-5604. doi: 10.1021/jacs.0c13317. Epub 2021 Apr 6.

Abstract

Catalytic asymmetric Mannich reactions of imines with weakly acidic simple amides were developed using a chiral potassium hexamethyldisilazide (KHMDS)-bis(oxazoline) potassium salt (K-Box) catalyst system. The desired reactions proceeded to afford the target compounds in high yields with high diastereo- and enantioselectivities. It was suggested that a K enolate interacted with K-Box to form a chiral K enolate that reacted with imines efficiently. In this system, K-Box (potassium salt of Box) worked as a chiral ligand of the active potassium species.

Publication types

  • Research Support, Non-U.S. Gov't