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Synthesis 1990; 1990(12): 1153-1156
DOI: 10.1055/s-1990-27122
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Phosphoranaloge von Aminosäuren IV.1 Synthesen ungewöhnlicher 1-Aminophosphonsäuren über Diels-Alder-Reaktionen von (N-Acyliminomethyl)phosphonsäurediethylestern

Thomas Schrader* , Wolfgang Steglich
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Straße 1, D-5300 Bonn 1, Germany
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Publication Date:
02 May 2002 (online)

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Syntheses of Unusual 1-Aminophosphonic Acids via Diels-Alder Reactions of Diethyl (N-Acyliminomethyl)phosphonates (N-Acyliminomethyl)phosphonates 3 react with electron-rich dienes in (4 + 2)-cycloadditions either as dienophiles or as diene components to yield 3-(diethoxy)phosphoryl-2-azabicyclo[2.2.1] hept-5-enes 4 and 2-(diethoxy) phosphoryl-2,3-dihydro-4(1H)pyridone derivatives 6 or diethyl α-acylamino-γ-oxoalkylphosphonates 7 and 8, respectively. Ene-reactions of 3 with 2-phenyl-1-propene, acetylacetone and quadricyclane afford the corresponding adducts 9 in low yield.

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