Asymmetric synthesis of β-phosphono malonates via Fe2O3-mediated phospha-Michael addition to Knoevenagel acceptors

Organic Letters

Volumn 3, Issue 22, 2001, Pages 3515-3517

  Tedeschi, Livio ^a   Enders, Dieter ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; FERRIC ION; FERRIC OXIDE; MALONIC ACID DERIVATIVE; PHOSPHATE;

ARTICLE; CHEMISTRY; CONFORMATION; CRYSTALLIZATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRYSTALLIZATION; FERRIC COMPOUNDS; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MALONATES; MOLECULAR CONFORMATION; PHOSPHATES; STEREOISOMERISM;

EID: 0035516197     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016591v     Document Type: Article

References (39)

1. (a) Michaelis, A.; Kaehne, R. Ber. Dtsch. Chem. Ges. 1898, 31, 1048-1055.
2. (b) Arbusov, B. A. Pure Appl. Chem. 1964, 9, 307-335.
3. (a) Horiguchi, M.; Kandatsu, M. Nature 1959, 184, 901-902.
4. (b) Fields, S. C. Tetrahedron 1999, 55, 12237-12273.
5. (a) Hildebrand, R. The Role of Phosphonates in Living Systems; CRC Press: Boca Raton, 1983.
6. (b) Engel, R. Chem. Rev. 1977, 77, 349-367.
7. (c) Kafarski, P.; Lejczak, B. Phosphorus, Sulfur, Silicon Relat. Elem. 1991, 63, 193-215.
8. (a) Shipkowitz, N. L.; Bower, R. R.; Appell, R. N.; Nordeen, C. W. Appl. Microbiol. 1973, 26, 264-267.
9. (b) Mao, J. C. H.; Robishaw, E. E. Biochemistry 1975, 14, 5475-5479.
10. (c) Sabourin, C. L. K.; Reno, J. M.; Boezi, J. A. Arch. Biochem. Biophys. 1978, 187, 96-101.
11. (d) Mao, J. C. H.; Otis, E. R.; von Esch, A. M.; Herrin, T. R. Antimicrob. Agents Chemother. 1985, 27, 197-202.
12. Sandstrom, E. G.; Kaplan, J. C.; Byington, R. E.; Hirsch, M. S. Lancet 1985, 1, 1480-1482.
13. Patel, V. D.; Schmidt, R. J.; Biller, S. A.; Gordon, E. M.; Robinson, S. S.; Manne, V. J. Med. Chem. 1995, 38, 2906-2921.
14. Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119-144.
15. (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. 1997, 109, 1290-1310; Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1246.
16. (a) Shibasaki, M.; Sasai, H.; Arai, T. Angew. Chem. 1997, 109, 1290-1310; Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1246.
17. (b) Sasai, H.; Bougauchi, M.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 2717-2720.
18. (c) Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656-6657.
19. (d) Hanessian, S.; Bennani, Y. L.; Hervé Y. Synlett 1993, 35-36.
20. (e) Blazis, V. J.; Koeller, K. J.; Spilling, C. D. Tetrahedron: Asymmetry 1994, 5, 499-502.
21. (f) Devitt, P. G.; Kee, T. P. Tetrahedron 1995, 40, 10987-10996.
22. Enders, D.; Tedeschi, L.; Bats, J. W. Angew. Chem. 2000, 112, 4774-4776; Angew. Chem., Int. Ed. 2000, 39, 4605-4607.
23. Enders, D.; Tedeschi, L.; Bats, J. W. Angew. Chem. 2000, 112, 4774-4776; Angew. Chem., Int. Ed. 2000, 39, 4605-4607.
24. (a) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061.
25. (b) Leonard, J.; Díez_Barra, E.; Merino, S. Eur. J. Org. Chem. 1998, 63, 2051-2061.
26. (c) Rossiter, B. E.; Swingle, N. Chem. Rev. 1992, 92, 771-806.
27. (a) Beck, A. K.; Bastani, B.; Plattner, D. A.; Petter, W.; Seebach, D.; Braunschweig, H.; Gysi, P.; La Vecchia, L. Chimia 1991, 45, 238-244.
28. (b) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem. 2001, 113, 96-142; Angew. Chem., Int. Ed. 2001, 40, 92-138.
29. (b) Seebach, D.; Beck, A. K.; Heckel, A. Angew. Chem. 2001, 113, 96-142; Angew. Chem., Int. Ed. 2001, 40, 92-138.
30. Morita, T.; Okamoto, Y.; Sakurai, H Tetrahedron Lett. 1978, 28, 2523-2526.
31. (a) Semenzin, D.; Etemad-Moghadam, G.; Albouy, D.; Diallo, O.; Koenig, M. J. Org. Chem. 1997, 62, 2414-2422.
32. (b) Albouy, D.; Laspéras, M.; Etemad-Moghadam, G.; Koenig, M. Tetrahedron Lett. 1999, 40, 2311-2314.
33. Kabashima, H.; Tsuji, H.; Hattori, H. Appl. Catal., A 1997, 165, 319-325.
34. Choudary, B. M.; Kantam, M. L.; Reddy, C. V.; Figueras, F. Tetrahedron 2000, 56, 9357-9364.
35. (a) Tanabe, K.; Hölderich, W. F. Appl. Catal., A 1999, 181, 399-434.
36. (b) Hattori, H. Chem. Rev. 1995, 95, 537-538.
37. (c) Ono, Y.; Baba, T. Catal. Today 1997, 38, 321-337.
38. (d) Tungler, A.; Fodor, K. Catal. Today 1997, 37, 191-208.
39. (e) Barteau, M. A. Chem. Rev. 1996, 96, 1413-1430.