Serkan EYMUR, Mehmet GÖLLÜ, Ayhan Sıtkı DEMİR

Self-condensation reactions of acyl phosphonates: synthesis of tertiary O-protected a-hydroxyphosphonates

The self-condensation reaction of benzoyl dialkyl phosphonates was developed using cyanide ion as catalyst, affording versatile tertiary O-protected a-hydroxy phosphonates in moderate yield.

Anahtar Kelimeler:

Acyl phosphonates, tertiary a-hydroxy phosphonates, phosphonate-phosphate rearrangement

Self-condensation reactions of acyl phosphonates: synthesis of tertiary O-protected a-hydroxyphosphonates

The self-condensation reaction of benzoyl dialkyl phosphonates was developed using cyanide ion as catalyst, affording versatile tertiary O-protected a-hydroxy phosphonates in moderate yield.

Keywords:

Acyl phosphonates, tertiary a-hydroxy phosphonates, phosphonate-phosphate rearrangement,

PDF

___

Dellaria, J. F., Jr.; Maki, R. G.; Stein, H. H.; Cohen, J.; Whittern, D.; Marsh, K.; Hoffman, D. J.; Plattner, J. J.; Perun, T. J. J. Med. Chem. 1990, 33, 534–542.
Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912–3916.
Stowasser, B.; Budt, K. H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625–6628.
Pompliano, D. L.; Rands, E.; Schaber, M. D.; Mosser, S. D.; Anthony, N. J.; Gibbs, J. B. Biochemistry 1992, 31, 3800–3807.
Hohl, R. J.; Lewis, K. A.; Cermak, D. M.; Wiemer, D. F. Lipids 1998, 33, 39–46.
Sikorski, J. A.; Miller, M. J.; Braccolino, D. S.; Cleary, D. G.; Corey, S. D.; Font, J. L.; Gruys, K. J.; Han, C. Y.; Lin, K. C.; Pansegrau, P. D.; et al. Phosphorus Sulfur Silicon Relat. Elem. 1993, 76, 115–117.
Snoeck, R.; Holy, A.; Dewolf-Peeters, C.; Van Den Oord, J.; De Clercq, E.; Andrei, G. Antimicrob. Agents Chemother. 2002, 46, 3356–3361.
Peters, M. L.; Leonard, M.; Licata, A. A. Clev. Clin. J. Med. 2001, 68, 945–951.
Leder, B. Z.; Kronenberg, H. M. Gastroenterology 2000, 119, 866–869.
Huber, J. W.; Gilmore, W. F.; Robertson, L. W.; J. Med. Chem. 1975, 18, 106–108.
Atherton, F. R.; Hall, M. J.; Hassall, C. H.; Holmes, S.W.; Lambert, R.W.; Lloyd, J.; Ringrose, P. S. Antimicrob. Agents Chemother. 1980, 18, 897–905.
Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279–13332.
Kolodiazhnyi, O. I. Advances in Asymmetric Synthesis Vol. 3, JAI Press: London, 1998, 273.
Kolodiazhnyi, O. I. Russian Chemical Reviews 2006, 75, 227–253.
Engel, R. Synthesis of Carbon–Phosphorus Bonds, CRC Press: Boca Raton, FL, 1987.
Yokomatsu, T.; Yamagishi, T.; Shibuya, S. J. Chem. Soc., Perkin Trans. 1 1997, 1527–1533.
Wroblewski, A. E.; Balcerzak, K. B. Tetrahedron: Asymmetry 2001, 12, 427–431.
Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1993, 4, 1401–1404.
Rowe, B. J.; Spilling, C. D. Tetrahedron: Asymmetry 2001, 12, 1701–1708.
Arai, T.; Bougauchi, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1996, 61, 2926–2927.
Gajda, T. Tetrahedron: Asymmetry 1994, 5, 1965–1972.
Nesterov, V. V.; Kolodiazhnyi, O. I. Zh. Obshch. Khim. 2005, 75, 1225–1229.
Meier, C.; Laux, W. H. G. Tetrahedron: Asymmetry 1996, 7, 89–94.
Pogatchnik, D. M.; Wiemer, D. F. Tetrahedron Lett. 1997, 38, 3495–3498.
Yokomatsu, T.; Yamagishi, T.; Suemune, K.; Yoshida, Y.; Shibuya, S. Tetrahedron 1998, 54, 767–780.
Wiemer, D. F.; Kim, D. Y. Tetrahedron Lett. 2003, 44, 2803–2805.
Samanta, S.; Zhao, C.-G. J. Am. Chem. Soc. 2006, 128, 7442–7443.
Perera, S.; Naganaboina, V. K.; Wang, L.; Zhang, B.; Guo, Q.; Rout, L.; Zhao, C.-G. Adv. Synth. Catal. 2011, 10, 1729–1734.
Demir, A. S.; Reis, ¨ O.; Kayalar, M.; Eymur, S.; Reis, B. Synlett 2006, 19, 3329–3333.
Demir, A. S.; Reis, ¨ O.; ˙Igdir, A. C ¸ .; Esiring¨ u, ˙I.; Eymur, S. J. Org. Chem. 2005, 70, 10584–10587.
Demir, A. S.; Reis, ¨ O.; Esiring¨ u, I.; Reis, B.; Baris, S. Tetrahedron 2007, 63, 160–165.
Demir, A. S.; Reis, B.; Reis, ¨ O.; Eymur, S.; G¨ oll¨ u, M.; Tural, S.; Saglam, G. J. Org. Chem. 2007, 72, 7439–7442. Demir, A. S.; Eymur, S. J. Org. Chem. 2007, 72, 8527–8530.