Chiral Metal Salts as Ligands for Catalytic Asymmetric Mannich Reactions with Simple Amides
- 6 April 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 143 (15), 5598-5604
- https://doi.org/10.1021/jacs.0c13317
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.Funding Information
- Japan Agency for Medical Research and Development
- Japan Society for the Promotion of Science (17H06445, 17H06448)
- Japan Chemical Industry Association
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