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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 29, 1999 - Issue 8
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Original Articles

Solid Phase Acylation of Phosphonoacetates Synthesis of β-Keto Phosphonates from Polymer Bound Phosphonoacetate

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Pages 1271-1275 | Received 07 Sep 1998, Published online: 17 Sep 2007

References

  • Fruchtel , J. S. and Jung , G. 1996 . Angew. Chem. Int. Ed Engl. , 35 : 17 – 42 . Brown, R. Cont. Org. Syn. 1997, 216–237; Lam, K. S., Lebl, M., Krchnak, V.;Chem. Rev. 1997, 97 411–448; Parlow, J. J., Mischke, D. A., Woodard, S. S.;J. Org. Chem. 1997, 62 5908–5919; Parlow, J. J., Normansell, J. E.;Molecular Diversity 1995, 1 266–269
  • Nefzi , A. , Ostresh , J. M. and Houghten , R. A. 1997 . Chem. Rev. , 97 : 449 – 471 . Hermkens, P. H. H., Ottenheijm, H. C. J., Rees, D. C.;Tetrahedron 1997, 53 5643- 5678; Thompson, L. A., Ellman, J. A.;Chem. Rev. 1996, 96 555–600
  • Hamper , B. C. , Kolodziej , S. A. and Scates , A. M. 1998 . Tetrahedron Lett. , 39 : 2047 – 2050 . Sim, M. M., Lee, C. L., Ganesan, A.;Tetrahedron Lett. 1998, 39 2195–2198
  • Maryanoff , B. E. and Beitz , A. B. 1989 . Chem. Rev. , 89 : 863 – 927 . β-Keto phosphonates are valuable intermediates for organic synthesis, especially for the preparation of α, β-unsaturated carbonyl compounds by the Horner-Wadsworth-Emmons condition. For general reviews, see; Wadsworth, W. S. Jr.;Org. React- (N, Y) 1977, 25 73; Walker, B. J.;Organophosphorus Reagents in Organic Synthesis Cadogan, J. I. G. Ed Academic Press : New York, 1974, 155–206; Kelly, S. E.; In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Schreiber, S. L., Eds.; Pergamon Press : Oxford, 1991; Vol. 1, Chapter 3.1, pp 755–782
  • Kim , D. Y. , Kong , M. S. and Kim , T. H. 1996 . Synth. Commun. , 26 : 2487 – 2496 . Kim, D. Y., Kong, M. S., Lee, K.;J. Chem. Soc. Perkin Trans. 1. 1997, 1361–1363
  • General experimental procedure : To a stirred suspension of Wang resin (300mg, 1 mmol/g) in CH2CI2 (10 mL), diethyl phosphonoacetic acid (1 64 μmL, 0.4 mmol), DCC (104 mg, 0.5 mmol), HOBt (13.5 mg, 0.1 mmol) and triethylamine (63 μmL, 0.45 mmol) at room temperature, followed by stirring for 10 h. The resin 2 was washed (Et2O and EtOAc), dried. The loaded resin 2 (100 mg) was suspended in toluene (2 mL) and MgCk (10.7 mg, 0.11 mmol), triethylamine(42 μmL. 0.3 mmol) and carboxylic acid chloride (0.2 mmol) were added and stirred for 12 h at room temperature. The resin 3 was washed (CH2Cl2 and EtOAc), resuspended in 2 mL of TFA/ CH2Cl2 (1:1) for 30 min. The filtrate was pooled with resin washing (CH2Cl2 and EtOAc), concentrated, and chromatographed to give β-keto phosphonate 4

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