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

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.

A novel approach for obtaining α,β-diaminophosphonates bearing structurally diverse side chains and their interactions with transition metal ions studied by ITC

“…19,41,42 The detailed preparation of Boc-Gly-DAla-PO(OEt) 2 ( 5) is presented in a recently published paper. 43 Optimization of piperidine addition to phosphonodehydroalanine derivatives. The optimization of the reaction was performed based on piperidine addition to two phosphonodehydroalanine derivatives (Ac-DAla-PO(OEt) 2 and Z-DAla-PO(OEt) 2 ) in four solvent systems: dioxane, dioxane/H 2 O (1 : 1 v/ v), MeOH, MeOH/H 2 O (1 : 1 v/v).…”