Highly diastereoselective pinacol coupling of secondary aliphatic aldehydes induced by a catalytic system consisting of vanadium complex, chlorosilane, and zinc metal

Journal of Organic Chemistry

Volumn 63, Issue 9, 1998, Pages 2812-2813

  Hirao, Toshikazu ^a   Asahara, Motoki ^a   Muguruma, Yasuaki ^a   Ogawa, Akiya ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2442536248     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo980376j     Document Type: Letter

References (56)

1. (a) Grame, M. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, p 563.
2. Wirth, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 61.
3. Schreibmann, A. A. Tetrahedron Lett. 1970, 49, 4271.
4. (a) Mukaiyama, T.; Sato, T.; Hanna, J. Chem. Lett. 1973, 1041.
5. Tyrlik, S.; Wolochowicz, I. Bull. Chim. Soc. Fr. 1973, 2147.
6. McMurry, J. E.; Fleming, M. P. J. Am. Chem. Soc. 1974, 96, 4708.
7. Corey, E. J.; Danheiser, R. L.; Chandrasekaran, S. J. Org. Chem. 1976, 41, 260.
8. Suzuki, H.; Manabe, H.; Enokiya, R.; Hanazaki, Y. Chem. Lett. 1986, 1339.
9. Handa, Y.; Inanaga, J. Tetrahedron Lett. 1987, 28, 5717.
10. (g) McMurry, J. E. Chem. Rev. 1989, 89, 1513.
11. (h) Barden, M. C.; Schwartz, J. J. Am. Chem. Soc. 1996, 118, 5484.
12. (i) Balu, N.; Nayak, S. K.; Banerji, A. J. Am. Chem. Soc. 1996, 118, 5932.
13. (j) Clerici, A.; Clerici, L.; Porta, O. Tetrahedron Lett. 1996, 37, 3035.
14. (a) Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014.
15. Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924.
16. Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28.
17. Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
18. (a) Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1973, 935.
19. So, J.-H.; Park, M.-K.; Boudjouk, P. J. Org. Chem. 1988, 53, 5871.
20. Tanaka, K.; Kishigami, S.; Toda, F. J. Org. Chem. 1990, 55, 2981.
21. Tsukinoki, T.; Kawaji, T.; Hashimoto, I.; Mataka, S.; Tashiro, M. Chem. Lett. 1997, 235.
22. (a) Namy, J. L.; Kagan, H. B. Tetrahedron Lett. 1983, 24, 765.
23. Molander, G. A. Chem. Rev. 1992, 92, 29.
24. Taniguchi, N.; Kaneta, N.; Uemura, M. J. Org. Chem. 1996, 61, 6088.
25. (a) Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Guy, R. K.; Sorensen, E. J.; Claiborne, C. F.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634.
26. Shiina, I.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Saitoh, K.; Mukaiyama, T. Chem. Lett. 1997, 419.
27. (a) Kammermeier, B.; Beck, G.; Holla, W.; Jacobi, D.; Napierski, B.; Jendralla, H. Chem. Eur. J. 1996, 2, 307.
28. Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
29. Fürstner's group and our group have independently demonstrated the catalytic McMurry coupling reaction and pinacol coupling reaction, respectively; see: (a) Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
30. Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366.
31. Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. Abstracts for the 6th International Kyoto Conference on New Aspects of Organic Chemistry, 1994; p 175.
32. For quite recent advances in the catalytic pinacol coupling, see: (a) Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666.
33. Maury, O. Villiers, C. Ephritikhine, M. New J. Chem. 1997, 21, 137.
34. Gansäuer, A. J. Chem. Soc., Chem. Commun. 1997, 457.
35. Gansäuer, A. Synlett 1997, 363.
36. Lipski, T. A.; Hilfiker, M. A.; Nelson, S. G. J. Org. Chem. 1997, 62, 4566.
37. For the diastereoselective pinacol coupling of aliphatic aldehydes by using a stoichiometric Nb(III), see: Szymoniak, J.; Besançon, J.; Moïse, C. Tetrahedron 1994, 50, 2841.
38. 4
39. (a) Corey, E. J.; Danheiser, R. K.; Chandrasekaran, S. J. Org. Chem. 1977, 42, 2655.
40. McMurry, J. E.; Kees, K. L. J. Org. Chem. 1977, 42, 2655.
41. Molander, G. A.; Kenny, C. J. J. Org. Chem. 1988, 53, 2134.
42. McMurry, J. E.; Rico, J. G. Tetrahedron Lett. 1989, 30, 1169.
43. Raw, A. S.; Pedersen, S. F. J. Org. Chem. 1991, 56, 830.
44. Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125.
45. (g) Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1995, 117, 7283.
46. In the case of ketones, the formation of dioxolanes is very slow even in DME, and therefore, DME can be employed as a solvent for the catalytic pinacol coupling to give 1,2-diol. On the other hand, the catalytic pinacol coupling reaction in THF at temperatures over 45 °C was accompanied by a ring opening reaction of THF.
47. For the reductive intramolecular cyclization using stoichiometric amounts of SmI2, see: (a) Molander, G. A.; Kenny, C. J. Am. Chem. Soc. 1989, 111, 8236.
48. Molander, G. A.; Harring, L. J. Org. Chem. 1990, 55, 6171.
49. Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132
50. Inokuchi, T.; Kawafuchi, H.; Torii, S. J. Org. Chem. 1991, 56, 4983.
51. The same reaction at 20 °C provided 52% (R-Me/β-Me) 60/40) of 5 (trans-isomer) with the formation of its cis-isomer (ca. 20%).
52. Curran, D. P.; Porter, N. A.; Giese, B. In Stereochemistry of Radical Reactions; VCH Press: Weinheim, 1995.
53. Hirao, T.; Hirano, K.; Hasegawa, T.; Ohshiro, Y.; Ikeda, I. J. Org. Chem. 1993, 58, 6529.
54. For some other catalytic system of early transition metals, see, for example: (a) Fürstner, A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 2533.
55. Corey, E. J.; Zheng, G. Z. Tetrahedron Lett. 1997, 38, 2045.
56. For YbI2-catalyzed reduction with Al, see: Ogawa, A.; Ohya, S.; Sumino, Y.; Sonoda, N.; Hirao, T. Tetrahedron Lett. 1997, 38, 9017.