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Rh-catalyzed asymmetric hydrogenation of α- and β-enamido phosphonates: highly enantioselective access to amino phosphonic acids.

Hongyan Du

Published 2022 in Organic and biomolecular chemistry

ABSTRACT

Catalytic asymmetric hydrogenation of α- and β-enamido phosphonates was developed using a complex formed in situ through a chiral hybrid phosphine-bicyclic bridgehead phosphoramidite ligand and rhodium metal precursor as the catalyst. This strategy afforded a wide variety of substrates in excellent yield (96-99%) and enantiomeric excess (≤99%) with very low catalyst loading (S/C up to 10 000) and relatively mild reaction conditions. Further investigations suggested that the hydrogenation reaction occurred only at the CC bond of the enamido phosphate stage without tautomerization to the imine form. Tandem hydrolysis reactions of hydrogenated products gave the corresponding α- and β-amino phosphonic acids in fairly high yield, which could be multipurpose building blocks for bioorganic chemistry, medicinal chemistry and organic synthesis.

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