Controlling Factors Governing Catalytic Process: Asymmetric Allylation Reaction Promoted by BINOL-Zr(IV) Catalyst with Synergetic Reagent

Bulletin of the Korean Chemical Society

Volumn 18, Issue 5, 1997, Pages 471-473

  Yu, Chan Mo ^a   Choi, Ha Soon ^a   Jung, Won Hyuk ^a   Kim, Hyuk Jun ^a   Lee, Jeon Koo ^a  

^a Sungkyunkwan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031350598     PISSN: 02532964     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

1. For the comprehensive reviews, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31. (c) Santell, M.; Rons, J. M. Lewis Acids and Selectivity in Organic Chemistry; CRC Press: New York, 1996; pp 91-184.
2. For the comprehensive reviews, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31. (c) Santell, M.; Rons, J. M. Lewis Acids and Selectivity in Organic Chemistry; CRC Press: New York, 1996; pp 91-184.
3. For the comprehensive reviews, see: (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207. (b) Marshall, J. A. Chem. Rev. 1996, 96, 31. (c) Santell, M.; Rons, J. M. Lewis Acids and Selectivity in Organic Chemistry; CRC Press: New York, 1996; pp 91-184.
4. (a) Ishihara, K.; Mouri, M.; Gao, Q.; Maruyama, T.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1993, 115, 11490.
5. (b) Marshall, J. A.; Tang, Y. Synlett 1992, 653.
6. (c) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
7. (d) Costa, A. L.; Piazza, G. M.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Am. Chem. Soc. 1993, 115, 7001.
8. (e) Faller, J. W.; Sams, D. W.; Liu, X. J. Am. Chem. Soc. 1996, 118, 1217.
9. (f) Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723.
10. (g) Cozzi, P. G.; Orioli, P.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1997, 38, 145.
11. (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Son: New York, 1994.
12. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH; New York, 1993.
13. (a) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Lee, S.-S. Tetrahedron Lett. 1996, 37, 7095.
14. (b) Yu, C.-M.; Choi, H.-S.; Jung, W.-H.; Kim, H.-J.; Shin, J. J. Chem. Soc. Chem. Commun. 1997, 761.
15. (c) Yu, C.-M.; Yoon, S.-K.; Choi, H.-S.; Baek, K. J. Chem. Soc., Chem. Commun. 1997, 763.
16. Bedeshi, P.; Casolari, S.; Costa, A. L.; Tagliavini, E.; Umani-Ronchi, A. Tetrahedron Lett. 1995, 36, 7897.
17. 3B and i-PrSH, see: Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988, p 436. (b) Pelter, A.; Rowe, K.; Sharrocks, D. N.; Smith, K.; Subramanyam, C. J. J. Chem. Soc., Dalton Trans. 1976, 2087.
18. 3B and i-PrSH, see: Pelter, A.; Smith, K.; Brown, H. C. Borane Reagents; Academic Press: New York, 1988, p 436. (b) Pelter, A.; Rowe, K.; Sharrocks, D. N.; Smith, K.; Subramanyam, C. J. J. Chem. Soc., Dalton Trans. 1976, 2087.
19. The formation of primary alcohols from side reaction of corresponding aldehydes mediated by the Zr(IV) complex was a severe problem (up to 15%), see ref. 5.
20. Oxazaborolidines 6 proved to be effective catalysts for the chiral Lewis acid promoted reactions such as Diels- Alder and aldol reactions, see: (a) Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365. (d) Deloux, L.; Srebnik, M. Chem. Ber. 1993, 93, 763.
21. Oxazaborolidines 6 proved to be effective catalysts for the chiral Lewis acid promoted reactions such as Diels- Alder and aldol reactions, see: (a) Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365. (d) Deloux, L.; Srebnik, M. Chem. Ber. 1993, 93, 763.
22. Oxazaborolidines 6 proved to be effective catalysts for the chiral Lewis acid promoted reactions such as Diels- Alder and aldol reactions, see: (a) Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365. (d) Deloux, L.; Srebnik, M. Chem. Ber. 1993, 93, 763.
23. Oxazaborolidines 6 proved to be effective catalysts for the chiral Lewis acid promoted reactions such as Diels- Alder and aldol reactions, see: (a) Kiyooka, S.; Kaneko, Y.; Komura, M.; Matsuo, H.; Nakano, M. J. Org. Chem. 1991, 56, 2276. (b) Corey, E. J.; Loh, T.-P. J. Am. Chem. Soc. 1991, 113, 8966. (c) Parmee, E. R.; Tempkin, O.; Masamune, S. J. Am. Chem. Soc. 1991, 113, 9365. (d) Deloux, L.; Srebnik, M. Chem. Ber. 1993, 93, 763.