Enantio-enriched α-aminophosphonates (α-APs) are important building blocks in peptidomimetics and valuable bioisosteres of α-amino acids. The asymmetric catalytic synthesis of chiral α-APs has been previously explored mainly with aryl substrates and using non-commercially available organocatalysts or ligands. Herein we investigate a transfer hydrogenation strategy to convert the C=C of enamidophosphonates to α-APs using a commercially available rhodium catalyst and ligand. (Hetero)aryl and alkyl substituted α-APs have been produced with moderate to good ee%. Both the advantages and limitations of this methodology will be discussed.

Asymmetric synthesis of α-aminophosphonates (α-APs) by rhodium-catalyzed transfer hydrogenation

ACS Fall 2021

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.