Oxovanadium(IV) complex-mediated catalysis in Mukaiyama-type aldol additions

Synlett

Volumn , Issue 6, 1999, Pages 816-818

  Chen, Chien Tien ^a   Hon, Sang Wen ^a   Weng, Shiue Shien ^a  

^a NATIONAL TAIWAN NORMAL UNIVERSITY   (Taiwan)

Author keywords

2,2' biphenol; Diastereoselective; Lewis acids; N methylimidazole; hydroxyesters

Indexed keywords

PHENOL DERIVATIVE; VANADIUM DERIVATIVE; VANADYL SULFATE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033002819     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2729     Document Type: Article

References (45)

1. (a) Mukaiyama, T. Org. React, 1982, 28, 203.
2. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
3. (c) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984, Vol. 3, Chapter 2.
4. (d) Mukaiyama. T.; Murakami, M. Croat. Chem. Acta 1986, 59, 221.
5. (e) Gennari, C. In Comprehensive Organic Synthesis: Additions to C-X π-Bonds Part 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; Chapter. 2, 4.
6. (f) Denmark, S. E.; Chen, C.-T. Tetrahedron Lett. 1994, 35, 4327.
7. (a) Nelson, S. G. Tetrahedron Asymmetry 1998, 9, 357.
8. (b) Chen, C.-T.; Chao, S.-D.; Yen, K.-C.; Chen, C.-H.; Chou, I.-C.; Hon, S.-W. J. Am. Chem. Soc. 1997, 119, 11341 and references therein.
9. (a) Kobayashi, S.; Hachiya, I.; Ishitani, H.; Araki, M. Synlett 1993, 472.
10. (b) For rare earth metal complexes, see: Kobayashi, S. Synlett 1994, 689.
11. (a) Hollis, T. K.; Bosnich, B. J. Am. Chem. Soc. 1995, 117, 4570.
12. (b) Carreira, E. M.; Singer, R. A. Tetrahedron Lett. 1994, 35, 4323.
13. Mukaiyama, T.; Akamatsu, H.; Han, J. S. Chem. Lett. 1990, 889.
14. (a) Bach, T.; Fox, D. N. J. Chem. Soc. Chem. Commun. 1992, 1634.
15. (b) Colombo, L.; UIgheri, F. Tetrahedron Lett. 1989, 30, 6435.
16. Kobayashi, S.; Busujima, T.; Nagayama, S. Tetrahedron Lett. 1998, 39, 1579.
17. (a) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814.
18. (b) Evans, D. A.; Kozlowski, M. C.; Burgey, C. S.; MacMillan, D. W. C. J. Am. Chem. Soc. 1997, 119, 7893.
19. (a) For a review of vanadium in synthesis, see: Hirao, T. Chem. Rev. 1997, 97, 2707.
20. (b) For the only documented example on the use of V(IV) in aymmetric Diels-Alder reactions, see: Togni, A. Organometallics 1990, 9, 3106.
21. (c) Togni, A.; Rist, G.; Rihs, G.; Schweiger, A. J. Am. Chem. Soc. 1993, 115, 1908.
22. (a) Nakajima, K.; Kojimo, M.; Fujita, J. Chem. Lett. 1986, 1483.
23. (b) Takai, T.; Yamada, T.; Mukaiyama, T. Chem. Lett. 1990, 1657.
24. (c) Bolm, C.; Bienewald, F. Angew. Chem. Int. Ed. Engl. 1995, 34, 2640.
25. Vilas Boas, L.; Costa Pessoa, J. In Comprehensive Coordination Chemistry, Wilkinson, G., Gillard, R. D., McCleverty, J. A., Eds.; Pergamon: Oxoford, England, 1987, Vol. 3, p453.
26. (a) Dichmann, K.; Harner, G.; Nyburg, S. C.; Reynold, S. W. F. J. Chem, Soc. D. 1970, 1295.
27. (b) For DMSO complexes, see: Agarwal, K.; Singh, G. J. Ind. Chem. Soc. 1986, 63, 926.
28. (a) Hara, R.; Mukaiyama, T. Chem. Lett. 1989, 1909.
29. (b) Mukaiyama, T.; Hara, R. Chem. Lett. 1989, 1171.
30. (c) Mukaiyama, T.; Inubushi, A.; Suda, S.; Hara, R.; Kobayashi, S. Chem. Lett. 1990, 1015.
31. (d) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem. Lett. 1994, 97.
32. (a) Sinha, A. K.; Kumari, U.; Singh, C. P.; Mishra, L. K. J. Ind. Chem. Soc. 1990, 67.
33. (b) Cornman, C. R.; Kampf, J.; Lab, M. S.; Pecoraro, V. L. Inorg. Chem. 1992, 31, 2035.
34. (c) Nath, P. K.; Misra, N. C.; Chakravortty, V.; Dash, K. C. Polyhedron 1987, 6, 455.
35. Turevskaya, E. P.; Turova, N. Y. J. Gen. Chem. USSR 1988, 58, 1441.
36. (a) Selbin, J.; Holmes, L. H. J. Inorg. Nucl. Chem. 1962, 24, 1111.
37. (b) Bristow, S.; McAvilley, S. C. M.; Clegg, W. Polyhedron 1989, 8, 87.
38. 3 as a base.
39. Chen, C.-T.; Chao, S.-D.; Yen, K.-C. Synlett, 1998, 924.
40. (a) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 1997, 119, 7153.
41. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
42. (c) Heller, D. P.; Goldberg, D. R.; Wulff, W. D. J. Am. Chem. Soc. 1997, 119, 10551.
43. 4-mediated aldol reaction: Tomo, Y.; Yamamoto, K. Tetrahedron Lett. 1985, 26, 1061.
44. Similar results were obtained when reactions were performed in the presence of MS 4Å. For the effect of MS, see: Iida, T.; Yamamoto, N.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1997, 119, 4783.
45. Chiral vanadyl complexes derived from BINOL and camphor were found to catalyze the aldol reactions with poor enantiomeric excesses (< 10%). Chen, C.-T.; Hon, S.-W.; Weng, S.-S. unpublished results.