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Synthesis 1993; 1993(10): 968-972
DOI: 10.1055/s-1993-25982
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1,8-Diazabicyclo[5.4.0]undecene Mediated Transesterification of p-Nitrophenyl Phosphonates: A Novel Route to Phosphono Esters

Dan S. Tawfik* , Zelig Eshhar, Alfonso Bentolila, Bernard S. Green
  • *Department of Chemical Immunology, Weizmann Institute of Science, Reohovot 76 100, Israel and Department of Pharmaceutical Chemistry, Faculty of Medicine, Hebrew University, P.O. Box 12065, Jerusalem 91120, Israel
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Publikationsdatum:
29. April 2002 (online)

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DBU (1,8-diazabicyclo[5.4.0]undecene) was found to efficiently mediate the transesterification of p-nitrophenyl (PNP) phosphonates by various alcohols. The reactions of bis-PNP phosphonates in the presence of DBU, using both primary and secondary alcohols, phenols and amines, proceed rapidly and with high yield to afford the corresponding monoalkyl/aryl mono-PNP phosphonates as sole products (1, Scheme 2). The resulting monoalkyl/aryl mono-PNP phosphonates can be further reacted with a second alcohol to give the corresponding differently disubstituted phosphonates 3, or selectively hydrolysed to yield the monoalkyl/aryl phosphonic acids 2. We have applied this chemistry to the preparation of a series of phosphono ester transition state analogues 11a-e (Scheme 3) that were used as haptens for raising catalytic antibodies.