Access to α-Aminophosphonic Acid Derivatives and Phosphonopeptides by [Rh(P-OP)]-Catalyzed Stereoselective Hydrogenation

J Org Chem. 2020 Nov 20;85(22):14779-14784. doi: 10.1021/acs.joc.0c00914. Epub 2020 Jun 30.

Abstract

The hydrogenation of N-substituted vinylphosphonates using rhodium complexes derived from P-OP ligands L1, ent-L1, or (R,R)-Me-DuPHOS as catalysts has been successfully accomplished, achieving very high levels of stereoselectivity (up to 99% ee or de). The described synthetic strategy allowed for the efficient preparation of α-aminophosphonic acid derivatives and phosphonopeptides, which are valuable building blocks for the preparation of biologically relevant molecules.

Publication types

  • Research Support, Non-U.S. Gov't