Allylation of unactivated ketones by tetraallyltin accelerated by phenol. Application to asymmetric allylation using a tetraallyltin-BINOL system

Chemistry Letters

Volumn , Issue 8, 1998, Pages 743-744

  Yasuda, Makoto ^a   Kitahara, Noriko ^a   Fujibayashi, Tatsuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0032334348     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.743     Document Type: Article

References (40)

1. For example: a) A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, and F. Schwarzenbach, J. Am. Chem. Soc., 114, 2321 (1992).
2. b) A. L. Costa, M. G. Piazza, E. Tagliavini, C. Trombini, and A. Umani-Ronchi, J. Am. Chem. Soc., 115, 7001 (1993).
3. c) G. E. Keck, K. H. Tarbet, and L. S. Geraci, J. Am. Chem. Soc., 115, 8467 (1993).
4. d) J. W. Faller, D. W. I. Sams, and X. Liu, J. Am. Chem. Soc., 118, 1217 (1996).
5. e) A. Yanagisawa, H. Nakashima, A. Isniba, and H. Yamamoto, J. Am. Chem. Soc., 118, 4723 (1996).
6. f) M. Nishida, T. Tozawa, K. Yamada, and T. Mukaiyama, Chem. Lett., 1994, 1125.
7. g) K. Furuta, M. Mouri, and H. Yamamoto, SYNLETT, 1991, 561.
8. h) K. Ishihara, M. Mouri, Q. Gao, T. Maniyama, K. Furuta, and H. Yamamoto, J. Am. Chem. Soc., 115, 11490 (1993).
9. i) L. C. Zhang, H. Sakurai, and M. Kira, Chem. Lett., 1997, 129.
10. j) Z. Wang, D. Wang, and X. Sui, Chem. Commun., 1996, 2261.
11. k) D. R. Gauthier, Jr., and E. M. Carreira, Angew. Chem., Im. Ed. Engl., 35, 2363 (1996).
12. l) S. E. Denmark. D. M. Coe, N. E. Pratt, and B. D. Griedel, J. Org. Chem., 59, 6161 (1994).
13. m) R. M. Angell, A. G. M. Barren, D. C. Braddock, S. Swallow, and B. D. Vickery, Chem. Commun., 1997, 919.
14. n) Z. Y. Wei, J. S. Li and T. H. Chen, J. Org. Chem., 54, 5768 (1989).
15. o) T. K. M. Shing, and L.-H. Li, J. Org. Chem., 62, 1230 (1997).
16. The enantioselective allylboration of ketones with oxidation to give enantiomeric homoallylic alcohols: P. K. Jadhav, K. S. Bhat, T. Perumal, and H. C. Brown, J. Org. Chem., 51, 432 (1986).
17. a) I. Ojima, Y. Miyazawa, and M. Kumagai, J. Chem. Soc., Chem Commun., 1976, 927.
18. b) K. Soai, M. Ishizaki, and S. Yokoyama, Chem. Lett. 1987, 341.
19. c) K. Yamada, T. Tozawa, M. Nishida, and T. Mukaiyama, Bull. Chem Soc. Jpn., 70, 2301 (1997).
20. a) L. F. Tietze, K. Schiemann, and C. Wegner, J. Am. Chem. Soc. 117, 5851 (1995).
21. b) L. F. Tietze, C. Wegner, and C. Wulff, SYNLETT, 1996, 471.
22. For example: a) Y. Yamamoto, T. Komatsu, and K. Maruyama, J. Chem. Soc., Chem. Commun., 1983, 191.
23. b) E. W. Abel, and R. J. Rowley, J. Organomet. Chem., 84, 199 (1975).
24. c) V. Peruzzo and G. Tagliavini, J. Organomet. Chem., 162, 37 (1978).
25. d) A. Gambaro, V. Peruzzo, G. Plazzogna, and G. Tagliavini, J. Organomet. Chem., 197, 45 (1980).
26. e) A. Gambaro, D. Marton, V. Peruzzo, and G. Tagliavini, J Organomet. Chem., 204, 191 (1981).
27. f) T. Mukaiyama, T. Harada, Chem. Lett., 1981, 1527.
28. g) M. Yasuda, Y. Sugawa, A. Yamamoto, I. Shibata, and A. Baba, Tetrahedron Lett., 37, 5951 (1996).
29. a) M. Yasuda, K. Hayashi, Y. Katoh, I. Shibata, and A. Baba, J. Am Chem. Soc . 120, 715 (1998).
30. b) I. Shibata and A. Baba, Org. Prep. Proc. Int., 26, 85 (1994).
31. c) K. Yano, Y. Hatta, A. Baba, and H. Matsuda, SYNLETT, 1991, 555.
32. d) K. Yano, Y. Hatta, A. Baba, and H. Matsuda, Synthesis, 7, 693 (1992).
33. e) T. Kawakami, I. Shibata, and A. Baba, J. Org. Chem., 61. 82 (1996).
34. a) T. M. Cokley, P. J. Harvey, R. L. Marshall, A. McCluskey, and D. J. Young, J. Org Chem., 61, 1961 (1997).
35. b) T. M. Cokley, R. L. Marshall, A. McCluskey, and D. J. Young, Tetrahedron Lett., 37, 1905 (1996).
36. a) M. Yasuda, T. Fujibayashi, I. Shibata, and A. Baba, 70th Annual Meeting of the Chemical Society of Japan, March 1996, Abstr., No. 1J226.
37. b) M. Yasuda, T. Fujibayashi, and A. Baba, 43rd Symposium on Organometallic Chemistry, Japan, 1996, Abstr., B207.
38. A. Yanagisawa, H. Inoue, M. Morodome, and H. Yamamoto, J. Am. Chem. Soc., 115, 10356 (1993).
39. iPrOH instead of phenol failed. A trace amount of 3 was obtained under the same conditions.
40. The absolute configuration was determined by comparison of the optical rotation with that reported in the literature (Ref. 3b).