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Synthesis 1995; 1995(5): 539-543
DOI: 10.1055/s-1995-3942
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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

Elisabeth Öhler* , Silvia Kanzler
  • *Institut für Organische Chemie der Universität Wien, A-1090 Wien, Währinger Straße 38, Austria, Fax +43(1)313672280
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Publikationsdatum:
31. Dezember 2000 (online)

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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