New homochiral cyclic diol ligands for titanium alkoxide catalyzed phosphonylation of aldehydes

Tetrahedron Letters

Volumn 39, Issue 31, 1998, Pages 5485-5488

  Groaning, Michael D ^a   Rowe, Bradley J ^a   Spilling, Christopher D ^a  

^a UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYPHOSPHONATE; PHOSPHONIC ACID DERIVATIVE; TITANIUM ALKOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHIRALITY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032581679     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01139-3     Document Type: Article

References (48)

1. 1. a) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5587;
2. b) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E. Tetrahedron Lett. 1990, 31, 5591;
3. c) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, Jr., E. W. J. Med. Chem. 1995, 38, 4557;
4. d) 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.; Ream, J. E., Schnur, D.; Shah, A.; Walker, M. C. Phosphorus, Sulfur and Silicon 1993, 76, 115;
5. e) Peterson, M. L.; Corey, S. D.; Sikorski, J. A.; Walker, M. C Abstracts of Papers, 203rd American Chemical Society National Meeting, San Francisco, 1992, ORGN 469;
6. f) Stowasser, B.; Budt, K-H.; Jian-Qi, L.; Peyman, A.; Ruppert, D. Tetrahedron Lett. 1992, 33, 6625;
7. g) Moore, M. L.; Dreyer, G. B. Perspectives in Drug Discovery and Design 1993, 1, 85;
8. h) Wang, C-L. J.; Taylor, T. L.; Mical, A. J.; Spitz, S.; Reilly, T. M. Tetrahedron Lett. 1992, 33, 7667.
9. 2. a) Shabany, H.; Spilling, C.D. Tetrahedron Lett. 1998, 39, 1465;
10. b) De la Cruz, M.A.; Ph.D. Dissertation, University of Missouri-St. Louis, 1995;
11. c) Blazis, V. J.; De la Cruz, A.; Koeller, K. J.; Spilling, C. D. Abstracts, 206th National Meeting of the American Chemical Society, Chicago, IL, Aug. 22-27, 1993, ORGN 164;
12. d) Öhler, E.; Kotzinger, S. Synthesis 1993, 497;
13. e) Öhler, E; Kanzler, S. Liebigs Ann. Chem. 1997, 1437;
14. f) Zhu, J.; Lu, X. Tetrahedron Lett. 1987, 28, 1897;
15. g) Zhu, J.; Lu, X. J. Chem. Soc., Chem. Commun. 1987, 1318;
16. h) Cooper, D.; Trippett, S. J. Chem. Soc. Perkin 1 1981, 2127;
17. i) Koszuk, J.F. Syn. Commun. 1995, 25, 2533.
18. 3. Wiemer, D.F. Tetrahedron 1997, 53, 16609 and references cited therein.
19. 4. a) Wynberg, H.; Smaardijk, A. A. Tetrahedron Lett., 1983, 24, 5899;
20. b) Gajda, T. Tetrahedron Asymm. 1994, 5, 1965;
21. c) Meier, C.; Laux, W. H. G. Tetrahedron Asymm. 1995, 6, 1089;
22. d) Pogatchnik, D. M.; Wiemer, D. F. Tetrahedron Lett. 1997, 38, 3495;
23. e) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron Asymm. 1995, 6, 365;
24. f) Drescher, M.; Li F-Y.; Hammerschmidt, F. Tetrahedron 1995, 51, 4933;
25. g) Li Y.-F.; Hammerschmidt F. Tetrahedron Asymm. 1993, 4, 109;
26. h) Heisler A.; Rabiller, C.; Douillard, R.; Goalou, N.; Hägele, G.; Levayer, F. Tetrahedron Asymm. 1993, 4, 959;.
27. 5. a) Rath, N. P; Spilling, C. D. Tetrahedron Lett. 1994, 35, 227;
28. b) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron Asymm. 1993, 4, 1779;
29. c) Sasai, H.; Bougauchi, M.; Arai, T.; Shibasaki, M. Tetrahedron Lett. 1997, 38, 2717
30. d) Yokomatsu, T.; Yamagishi, T.; Shibuya S. J. Chem. Soc.. Perkin Trans. 1 1997, 1527;
31. e) Yokomatsu, T.; Yamagishi, T.; Shibuya, S. Tetrahedron Asymm. 1993, 4, 1783;
32. f) Arai, S.; Bougauchi, M.; Sasai, H.; Shibisaki, M. J. Org. Chem. 1996, 61, 2926.
33. 6. a) Koeller, K.J., Ph.D. Dissertation University of Missouri-St. Louis, 1993;
34. b) Groaning, M.D., M.S. Thesis, University of Missouri, 1996.
35. 7. a) Blazis, V. J.; Koeller, K. J.; Spilling, C. D. J. Org. Chem. 1995, 60, 931;
36. b) Blazis, V. J.; Koeller, K. J.; Rath, N.P. Spilling, C. D. Acta Cryst. 1997, B53, 838.
37. 8. a) Kozlowski, J. K, Rath, N. P.; Spilling, C. D. Tetrahedron 1995, 51, 6385;
38. b) Pirkle, W.H.; Brice, L.J.; Widlanksi, T.S.; Roestamadji, J. Tetrahedron Asymm. 1996, 7, 2173.
39. 9. The addition of diethyl phosphite to cinnamaldehyde proceeded with a higher enantiomeric excess (33%).
40. 10. Finn, M.G.; Sharpless, K.B. Asymmetric Synthesis 1985, 5, 247.
41. 11. Sharpless, K.B.; Amberg, W.; Bennani, Y.L.; Crispino, G.A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z-M; Xu, D.; Zhang, X-L; J. Org Chem. 1992, 57, 2768.
42. 12. Mannitol 1,2,4,6-bisacetonide and threitol 1,4 dibenzoate gave enantiomeric excesses of 7 and 0%, respectively.
43. 13. For example see; RajanBabu, T.V.; Casalnuovo, A.L. J. Am. Chem. Soc. 1992, 114, 6265; RajanBabu, T.V.; Ayers, T.A.; Casalnuovo, A.L. J. Am. Chem. Soc. 1994, 116, 4101; Duthaler, R. O.; Hafner, A.; Riediker, M. Pure & Appl. Chem. 1990, 62, 631.
44. 13. For example see; RajanBabu, T.V.; Casalnuovo, A.L. J. Am. Chem. Soc. 1992, 114, 6265; RajanBabu, T.V.; Ayers, T.A.; Casalnuovo, A.L. J. Am. Chem. Soc. 1994, 116, 4101; Duthaler, R. O.; Hafner, A.; Riediker, M. Pure & Appl. Chem. 1990, 62, 631.
45. 13. For example see; RajanBabu, T.V.; Casalnuovo, A.L. J. Am. Chem. Soc. 1992, 114, 6265; RajanBabu, T.V.; Ayers, T.A.; Casalnuovo, A.L. J. Am. Chem. Soc. 1994, 116, 4101; Duthaler, R. O.; Hafner, A.; Riediker, M. Pure & Appl. Chem. 1990, 62, 631.
46. 14. Zymanczyk-Duda, E.; Skwarczynski, M.; Lejczak, B.; Karfarski, P. Tetrahedron Asymm. 1996, 7, 1277.
47. 15. a) Crout, D.H.G.; Gaudet, V.S.B.; Laumen, K.; Schneider, M.P. J. Chem. Soc., Chem Commun. 1986, 808;
48. b) Seemayer, R.; Schneider, M.P. J. Chem. Soc., Chem. Commun. 1991, 49.