Regioselective Palladium(0) Catalyzed Amination of Carbonates of Allylic α-Hydroxyphosphonates with Hydroxylamine Derivatives: A Convenient Route to Phosphonic Acids Related to the Antibiotic Fosmidomycin

All articles of this category Palladium(0) catalyzed amination of diisopropyl (1-methoxycarbonyloxy-2-propenyl)phosphonate (1) with tert -butyl ( tert -butoxycarbonyloxy)carbamate (BocNHOBoc, 2a ), and ( N -acetyloxy)acetamide (AcNHOAc, 2b ) proceeds regiospecifically and with high ( E )-stereoselectivity to give the protected [3-( N -hydroxyamino)-1-propenyl]phosphonates 3a and 3b , respectively, in high yields. Hydrogenation of compounds 3a and 3b affords the corresponding propylphosphonates 4 . Compounds 3a,b and 4a,b are further converted to precursors and analogues of the phosphonic acid antibiotic fosmidomycin. phosphonate-substituted allylic carbonates - 1,3-interchange of functionality - Pd(0) catalysis - N -hydroxyamination - fosmidomycin