The synthesis, structure and properties of diazaphospholes: Reagents and ligands for asymmetric synthesis

Tetrahedron

Volumn 54, Issue 35, 1998, Pages 10513-10524

  De La Cruz, Antonette ^a   Koeller, Kevin J ^a   Rath, Nigam P ^a   Spilling, Christopher D ^a   Vasconcelos, Isabel C F ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; COMPLEX FORMATION; METAL BINDING; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032572849     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00502-X     Document Type: Article

References (54)

1. 1. Blazis, V.J.; Koeller, K.J.; Spilling, C.D. J. Org. Chem. 1995, 60, 931; Blazis, V.J.; Koeller, K.J.; Spilling, C.D. Tetrahedron Asymm. 1994, 5, 499; Rath, N.P; Spilling, C.D. Tetrahedron Lett. 1994, 35, 227.
2. 1. Blazis, V.J.; Koeller, K.J.; Spilling, C.D. J. Org. Chem. 1995, 60, 931; Blazis, V.J.; Koeller, K.J.; Spilling, C.D. Tetrahedron Asymm. 1994, 5, 499; Rath, N.P; Spilling, C.D. Tetrahedron Lett. 1994, 35, 227.
3. 1. Blazis, V.J.; Koeller, K.J.; Spilling, C.D. J. Org. Chem. 1995, 60, 931; Blazis, V.J.; Koeller, K.J.; Spilling, C.D. Tetrahedron Asymm. 1994, 5, 499; Rath, N.P; Spilling, C.D. Tetrahedron Lett. 1994, 35, 227.
4. 2. Synthesis of Carbon-Phosphorus Bonds, Engel, R., CRC Press, 1987.
5. 3. For previous examples see; Hoppe, I.; Schöllkopf, U.; Nieger, M.; Egert, E. Angew. Chem. Int. Ed. Engl. 1985, 24, 1067; Schollköpf, U.; Schütz, R. Liebigs Ann. Chem. 1987, 45.
6. 3. For previous examples see; Hoppe, I.; Schöllkopf, U.; Nieger, M.; Egert, E. Angew. Chem. Int. Ed. Engl. 1985, 24, 1067; Schollköpf, U.; Schütz, R. Liebigs Ann. Chem. 1987, 45.
7. 4. Koeller, K.J.; Spilling, C.D. Tetrahedron Lett. 1991, 32, 6297.
8. 5. a) Asperger, R.G.; Liu, C.F. Inorganic Chem. 1965, 4, 1492;
9. b) Larrow, J.F.; Jacobsen, E.N.; Gao, Y.; Hong, Y.; Nie, X.; Zepp, C. J. Org. Chem., 1994, 59, 1939;
10. c) Barluenga, J.; Alonso-Cires, L.; Asensio, G. Synthesis 1979, 962;
11. d) Mangeney, P.; Tejero, T.; Alexakis, A.; Grosjean, F.; Normant, J. Synthesis 1988, 255;
12. e) Cooley, W.E.; Liu, C.H.; Bailar, Jr., J.C. J. Am. Chem. Soc. 1959, 81, 4189;
13. f) Dickey, F.H.; Fickett, W.; Lucas, H.J. J. Am. Chem. Soc. 1952, 74, 944;
14. g) Corey, E.J.; Imwinkelried, R.; Pikul, S.; Xjang, Y.B. J. Am. Chem. Soc. 1989, 111, 5493;
15. h) Corey, E.J.; Jardine, P.D.; Virgil, S.; Yuen, P.W.; Connell, R.D. J. Am. Chem. Soc. 1989, 111, 9243.
16. 6. a) Hanessian, S.; Bennani, Y.L.; Delorme, D. Tetrahedron Lett. 1990, 31, 6461;
17. b) Hanessian, S.; Bennani, Y.L.; Tetrahedron Lett., 1990, 31, 6465;
18. c) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. J. Am. Chem. Soc. 1984, 106, 5754;
19. d) Hanessian, S.; Delorme, D.; Beaudoin, S.; Leblanc, Y. Chimica Scripta 1985, 88, 1419;
20. e) Hanessian, S.; Beaudoin, S. Tetrahedron Lett. 1992, 33, 7655;
21. f) Hanessian, S.; Beaudoin, S. Tetrahedron Lett. 1992, 33, 7659;
22. g) Hanessian, S.; Bennani, Y.L.; Hervé, Y. Synlett 1993, 35;
23. h) Hanessian, S.; Gomtsyan, A.; Payne, A.; Herve, Y.; Beaudoin, S. J. Org. Chem., 1993, 58, 5032;
24. i) Bennani, Y.L.; Hanessian, S. Chem. Rev. 1997, 97, 3161.
25. 7. a) Jongh, C.P.; Zwierzak, A.; Modro, T.A. Phosphorus, Sulfur, and Silicon 1991, 61, 205;
26. b) Nifant'ev, E.E.; Zavalishina, A.I. Zh. Obsch. Khim. 1967, 37, 1854;
27. c) Nifant'ev, E.E.; Shilov, I.V. Zh. Obsch. Khim. 1972, 42, 503;
28. d) Nifant'ev, E.E.; Shilov, I.V. Zh. Obsch. Khim. 1973, 43, 2654;
29. e) Nifant'ev, E.E.; Shilov, I.V. Zh. Obsch. Khim. 1975, 45, 1264;
30. f) Normant, H. Angew. Chem. Int. Ed. Engl. 1967, 6, 1050;
31. g) Corey, E.J.; Cane, D.E. J. Org. Chem. 1969, 34, 3053.
32. 8. a) Corbridge, D.E.; Pearson, M.S.; Walling, C. Topics in Phosphorus Chemistry, Vol 3, Interscience Publishers, 1966;
33. b) Fox, R.B.; Lockhart, L.B. The Chemistry of Organo-Phosphorus Compounds, Naval Research Laboratory, Washington D.C., 1948;
34. c) Hirao, T.; Masunaga, T.; Ohshiro, Y.; Agawa, T. Tetrahedron Lett. 1980, 21, 3595.
35. 9. a) Longeau, A.; Durand, S.; Spiegel, A.; Knochel, P. Tetrahedron Asymm. 1997, 8, 987;
36. b) Tye, H.; Smyth, D.; Eldrid, C.; Wills, M. J. Chem. Soc., Chem. Commun. 1997, 1053.
37. 10. Benson, S.C.; Cai, P.; Colon, M.; Haiza, M.A.; Tokles, M.; Snyder, J.K. J. Org. Chem. 1988, 55, 5335-41.
38. 11. Vasconcelos, I.C.F.; Anderson, G.K.; Rath, N.P.; Spilling, C.D. Tetrahedron Asymm. 1998, 9, 927.
39. 12. The relative sterochemistry for the cinnamaldehyde adduct of (R,R) 4e was S. The stereochemistry for the adducts of 4c and 4i was not determined. See reference 1.
40. 13. Allen, F.H.; Kennard, O.; Watson, D.G.; Brammer, L.; Orpen, A.G.; Taylor, R. J. Chem. Soc. Perkin Trans. II 1987, 1-19.
41. 14. a) Kevin J. Koeller, Nigam P. Rath and Christopher D. Spilling Acta Cryst. 1993, C49, 1547-1549;
42. b) Vincent J. Blazis, Kevin J. Koeller, Nigam P. Rath, and Christopher D. Spilling Acta Cryst. 1995, C51, 86-88.
43. 15. a) Bélanger-Gariépy, F.; Delorme, D., Hanessian, S.; Brisse, F. Acta Cryst. 1986, C42, 856;
44. b) Bélanger-Gariépy, F.; Bennani, Y.L.; Hanessian, S.; Brisse, F. Acta Cryst. 1989, C45, 289;
45. c) Bennani, Y.L.; Bélanger-Gariépy, F.; Hanessian, S. Acta Cryst. 1990, C46, 653;
46. d) Bennani, Y.L.; Hanessian, S. Acta Cryst. 1991, C47, 1230;
47. e) Bélanger-Gariépy, F.; Bennani, Y.L.; Beaudoin, S.; Hanessian S. Acta Cryst. 1992, C48, 1533;
48. f) Simard, M.; Beaudoin, S.; Hanessian, S. Acta Cryst. 1992, C48, 1535-1537.
49. 16. Kevin J. Koeller, Nigam P. Rath and Christopher D. Spilling Acta Cryst. 1993, C49, 1199-1201.
50. 17. De Jongh, C. P.; Modro, T. A. Phosphorus, Sulfur, and Silicon 1993, 79, 161.
51. 18. Koeller, K.J.; Rath, N.P.; Spilling, C.D. Phosphorus, Sulfur, and Silicon 1995, 103, 171.
52. 19. a) Alexakis, A.; Mutti, S.; Mangeney, P. J. Org. Chem. 1992, 57, 1224-37;
53. b) Alexakis, A.; Mutti, S.; Normant, J.F.; Mangeney, P. Tetrahedron Asymm. 1990, 1, 437.
54. 20. SHELXTL software package, Sheldrick, G. M., Siemens Analytical X-ray Division, Madison, WI, 1996.