Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P-C bond formation and hydrogenation.
Allylic acetates, formed by the acetylation of Baylis Hillman adducts, undergo addition of phosphorus nucleophiles to give stereoselectively the Z-unsaturated esters. TFA cleavage of the tert-butyl ester and asymmetric hydrogenation of the unsaturated acid yields the phosphono alkyl propanoic acid moiety, commonly found in phosphonate- and phosphinate-based enzyme inhibitors.
Badkar
Pallavi A
PA
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.
Rath
Nigam P
NP
Spilling
Christopher D
CD