Stereoselective pinacol coupling of (propargyl aldehyde)Co2(CO)6 complexes

Organometallics

Volumn 22, Issue 21, 2003, Pages 4260-4264

  Lake, K ^a   Dorrell, M ^a   Blackman, N ^a   Khan, M A ^a   Nicholas, K M ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIACETYLENIC DIOL COMPLEXES; PROPARGYL ALDEHYDE COMPLEXES; REDUCTANTS; STEREOSELECTIVE PINACOL COUPLING; X RAY STRUCTURES;

ALDEHYDES; COMPLEXATION; STEREOCHEMISTRY; STRUCTURE (COMPOSITION); X RAY ANALYSIS;

COBALT COMPOUNDS;

EID: 0142165762     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030392t     Document Type: Article

References (67)

1. Robertson, G. M. Pinacol Coupling Reactions. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Vol. 3, Pergamon Press: New York, 1991; pp 563-612.
2. Avalos, M.; Babiano, R.; Cintas, P.; Jimenez, J. L.; Palacios, J. C. Recent Research Developments in Organic Chemistry; 1997; Vol. 1, pp 159-178.
3. Wirth, T. Angew. Chem., Int. Ed. 1996, 35, 61.
4. Lipski, T. A.; Hilfiker, M. A.; Nelson, S. G. J. Org. Chem. 1997, 62, 4566.
5. Bandini, M.; Cozzi, P. G.; Morganti, S.; Umani-Ronchi, A. Tetrahedron Lett. 1999, 40, 1997.
6. Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666.
7. Gansauer, A. Chem. Commun. 1997, 457.
8. Gansauer, A.; Bauer, D. J. Org. Chem. 1998, 63, 2070.
9. Gansauer, A.; Bauer, D. Eur. J. Org. Chem. 1998, 2673.
10. Hirao, T.; Hatano, B.; Asahara, M.; Muguruma Y.; Ogawa, A. Tetrahedron Lett. 1998, 39, 5247.
11. Dunlap, M. S.; Nicholas, K. M. J. Organomet. Chem. 2001, 630, 125.
12. Dunlap, M.; Nicholas, K. M. Synth. Commun. 1999, 29, 1097.
13. Mukaiyama, T.; Yoshimura, N.; Igarashi, K.; Kagayama, A. Tetrahedron 2001, 57, 2499.
14. Groth, U.; Jeske, M. Angew. Chem., Int. Ed. 2000, 39, 574.
15. Yamamoto, Y.; Hattori, R.; Miwa, T.; Nakagai, Y.; Kubota, T.; Yamamoto, C.; Okamoto, Y.; Itoh, K. J. Org. Chem. 2001, 66, 3865.
16. Inanaga, J.; Hanada, Y. Tetrahedron Lett. 1987, 28, 5717.
17. Shimizu, M.; Goto, H.; Haykawa, R. Org. Lett. 2002, 4, 4097.
18. Durand, M. H. Compt. Rend. 1958, 246, 3469.
19. Piaux, L.; Durand, M. H. C. R. Acad. Sci. Chim. 1956, 243, 1774.
20. Durand, M. H. Compt. Rend. 1958, 246, 1562.
21. Melikyan, G. G.; Combs, R. C.; Lamirand, J.; Khan, M.; Nicholas, K. M. Tetrahedron Lett. 1994, 35, 363
22. Melikyan, G. G.; Khan, M.; Nicholas, K. M. Organometallics, 1995, 14, 2170.
23. Melikyan, G. G.; Deravakian, A.; Myer, S.; Yadegar, S.; Hardcastle, K. I.; Ciurash, J.; Toure, P. J. Organomet. Chem. 1999, 578, 68.
24. Gruselle, M.; Malezieux, B.; Andres, R.; Amouri, H.; Vaissermann, J.; Melikyan, G. G. Eur. J. Inorg. Chem. 2000, 2, 359.
25. Melikyan, G. G.; Deravakian, A. J. Organomet. Chem. 1997, 544, 143.
26. Salazar, K. L.; Khan, M. A.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 9053.
27. Salazar, K. L.; Nicholas, K. M. Tetrahedron 2000, 56, 2211.
28. Merlic, C. A.; Walsh, J. C. J. Org. Chem. 2001, 66, 2265.
29. Merlic, C. A.; Walsh, J. C. Tetrahedron Lett. 1998, 39, 2083.
30. Kuendig, E. P.; Ratni, H.; Crousse, B.; Bernardinelli, G. J. Org. Chem. 2001, 66, 1852.
31. Hoffmann, O.; Schmalz, H.-G. Synlett 1998, 12, 1426.
32. Schmalz, H.-G.; Siegel, S.; Schwarz, A. Tetrahedron Lett. 1996, 37, 2947.
33. Schmalz, H.-G.; Siegel, S.; Bats, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2383.
34. Merlic, C. A.; Walsh, J. C.; Tantillo, D. J.; Houk, K. N. J. Am. Chem. Soc. 1999, 121, 3596.
35. Merlic, C. A.; Hietbrink, B. N.; Houk, K. N. J. Org. Chem. 2001, 66, 6738.
36. Merlic, C. A.; Miller, M. M.; Hietbrink, B. N.; Houk, K. N. J. Am. Chem. Soc. 2001, 123, 4904.
37. Taniguchi, N.; Uemura, M. Tetrahedron 1998, 54, 12775.
38. Taniguchi, N.; Uemura, M. Tetrahedron Lett. 1998, 39, 5385.
39. Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088.
40. Ju, J.; Reddy, B. R.; Khan, M.; Nicholas, K. M. J. Org. Chem. 1989, 54, 5426.
41. Ganesh, P.; Nicholas, K. M. J. Org. Chem. 1993, 58, 5587.
42. Roush, W. R.; Park, J. C. Tetrahedron Lett. 1991, 32, 6285.
43. Clerici, A.; Porta, O. Tetrahedron Lett. 1982, 23, 3517.
44. Clerici, A.; Porta, O. Tetrahedron 1982, 38, 1293.
45. Clerici, A.; Porta, O.; Zago, P. Tetrahedron 1986, 42, 561.
46. Dunlap, M. S.; Nicholas, K. M. Synth. Commun. 1999, 29, 1097.
47. Annunziata, R.; Benaglia, M.; Cinquini, M.; Raimondi, L. Eur. J. Org. Chem. 1999, 3369, 9.
48. Pedersen, H. L.; Christensen, T. B.; Enemaerke, R. J.; Daasbjerg, K.; Skrydstrup, T. Eur. J. Org. Chem. 1999, 565, 5.
49. Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666.
50. Namy, J. L.; Souppe, J.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765.
51. Dickson, R. S.; Fraser, P. J. Advances in Organometallic Chemistry 12; Academic Press: New York, 1974; p 323.
52. Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 46, 5717.
53. Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
54. Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035.
55. Szymoniac, J.; Besancon, J.; Moise, C. Tetrahedron 1994, 50, 2841.
56. Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
57. Kempf, D. J.; Sowin, T. J.; Doherty, E. M.; Hannick, S. M.; Codavoci, L.; Henry, R. F.; Green, B. E.; Spanton, S. G.; Norbeck, D. W. J. Org. Chem. 1992, 57, 5692.
58. Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
59. Barden, M. C.; Schwartz, J. J. Org. Chem. 1997, 62, 7520.
60. 6 complexes; see: Schreiber, S. L.; Sammakia, T.; Crowe, W. E. J. Am. Chem. Soc. 1986, 108, 3128, and ref 14.
61. Peake, B. M.; Rieger, P. H.; Robinson, B. H.; Simpson, J. J. Am. Chem. Soc. 1980, 102, 156.
62. Arewgoda, M.; Rieger, P. H.; Robinson, B. H.; Simpson, J.; Visco, S. J. J. Am. Chem. Soc. 1982, 104, 5633.
63. Cundari, T. J. Chem. Inf. Comput. Sci. 1999, 39, 376.
64. Stuart, J. G.; Nicholas, K. M. Synthesis 1989, 6, 454.
65. Tester, R.; Varghese, V.; Montana, A. M.; Khan, M.; Nicholas, K. M. J. Org. Chem. 1990, 55, 186.
66. Ganesh, P.; Nicholas, K. M. J. Org. Chem. 1997, 43, 1737.
67. Bruker. SHELXTL, Version 5.1; Bruker AXS: Madison, WI, 1997.