Symmetry-Assisted Synthesis of C2-Symmetric trans-α,α'-Bis(hydroxymethyl)pyrrolidine and -piperidine Derivatives via Double Sharpless Asymmetric Dihydroxylation of αω-Terminal Dienes

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2224-2231

  Takahata, Hiroki ^a   Takahashi, Seiki ^a   Kouno, Shin Ichi ^a   Momose, Takefumi ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000758313     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971995f     Document Type: Article

References (47)

1. Whitesell, J. K. Chem. Rev. 1989, 89, 1581.
2. (a) Vigneron, J. P.; Dhaenens, M.; Horeau, A. Tetrahedron 1973, 29, 1055.
3. (b) Rautenstrauch, V. Bull. Soc. Chim Fr. 1994, 131, 515.
4. (a) Schreiber, S. L.; Schreiber, T. S.; Smith, D. B. J. Am. Chem. Soc. 1987, 109, 1525.
5. (b) Hoye, T.; Suhadolnik, J. C. J. Am. Chem. Soc. 1985, 107, 5312.
6. (c; Hoye, T.; Suhadolnik, J. C. Tetrahedron 1986, 42, 2855.
7. (a) Ramachandran, P. V.; Chen, G.-M.; Lu, Z.-H.; Brown, H. C. Tetrahedron Lett. 1996, 37, 3795.
8. (b) Schwink, L.; Knochel, P. Tetrahedron Lett. 1996, 37, 25.
9. (c) Chong, J. M.; Clarke, I. S.; Koch, L; Olbach, P. C.; Taylor, N. J. Tetrahedron: Asymmetry 1995, 6, 409.
10. (d) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S. Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629.
11. Soai, K.; Hori, H.; Kawahara, M. J. Chem. Soc., Chem. Commun. 1992, 106.
12. Kuwano, R.; Sawamura, M.; Shirai, J.; Takahashi, M.; Ito, Y. Tetrahedron Lett. 1995, 36, 5239.
13. Ramachandran, P. V.; Chen, G.-M.; Brown, H. C. Tetrahedron Lett. 1997, 38, 2417.
14. Aggarwal, V. K.; Evans, G.; Moya, E.; Dowden, J. J. Org. Chem. 1992, 57, 6390.
15. (a) Doi, T.; Hirabayashi, K.; Kokubo, M.; Komagata, T.; Yamamoto, K.; Takahashi, T. J. Org. Chem. 1996, 61, 8360.
16. (b) Muramatsu, H.; Kawano, H.; Ishii, Y.; Saburi, M.; Uchida, Y. J. Chem. Soc., Chem. Commun. 1989, 769.
17. Takahata, H.; Kouno, S.; Momose, T. Tetrahedron: Asymmetry 1995, 6, 1085.
18. (a) Hoye, T. R.; Ye, Z. J. Am. Chem. Soc. 1996, 118, 1801.
19. (b) Sauret, S.; Cuer, A.; Gourcy, J.-G.; Jeminet, G. Tetrahedron: Asymmetry 1995, 6, 1995.
20. Takahata, H. J. Synth. Org. Chem. Jpn. 1996, 54, 708.
21. Waldmann, H. In Organic Synthesis Highlight II; Waldmann, H., Ed.; VCH: Weinheim, 1995; p 49.
22. Kawanami, Y.; Ito, Y.; Kitagawa, T.; Taniguchi, Y.; Katsuki, T.; Yamaguchi, M. Tetrahedron Lett. 1984, 25, 857.
23. Yamamoto, Y.; Hoshino, J.; Fujimoto, Y.; Ohmoto, J.; Sawada, S. Synthesis 1993, 298.
24. Marzi, M.; Minetti, P.; Misti, D. Tetrahedron 1992, 48, 10127.
25. Sibi, M. P.; Lu, J. Tetrahedron Lett. 1994, 35, 4915.
26. (a) Najdi, S.; Kurth, M. J. Tetrahedron Lett. 1990, 31, 3279.
27. (b) Najdi, S.; Reichlin, D.; Kurth, M. J. J. Org. Chem. 1990, 55, 6241.
28. (c) McKew, J. C.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1994, 59, 3389.
29. (d) Moon, H.-S.; Eisenberg, S. W. E.; Wilson, M. E.; Schore, N. E., Kurth, M. J. J. Org. Chem. 1994, 59, 6504.
30. Hoshino, J.; Hiraoka, J.; Hata, Y.; Sawada, S.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1995, 693.
31. For an excellent review, see: Kolb, H. C.; VanNieuwenhze, M. S., Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
32. Crispino, G. A.; Jeong, K.-S.; Kolb, H. C.; Wang, Z.-M.; Xu, D.; Sharpless, K. B. J. Org. Chem. 1993, 58, 3785.
33. Hoye, T. R.; Tan, L. Synlett 1996, 615.
34. Becker, H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 448.
35. (a) Caddick, S.; Shanmugathasam, A.; Brasseur, D.; Delisser, V. M. Tetrahedron Lett. 1997, 38, 5735.
36. (b) Nakata, T.; Fukui, H.; Nakagawa, T.; Matsukura, H. Heterocycles 1996, 42, 159.
37. (c) Iwashita, M.; Kinsho, T.; Smith, A. B., III. Tetrahedron Lett. 1995, 36, 2199.
38. Oishi, T.; Shoji, M.; Kumahara, N.; Hirama, M. Chem. Lett. 1997, 845.
39. (a) Loza, E.; Lola, D.; Kemme, A.; Freimains, J. J. Chromatogr. A 1995, 708, 231.
40. (b) Dieter, P.; Taudien, S.; Samuel, O.; Kagan, H. B. J. Org. Chem. 1994, 59, 370.
41. (c) Camen, R. M.; Klica, K. D. Aust. J. Chem. 1991, 44, 895.
42. (d) Matsch, R.; Coors, C. Angew. Chem., Int. Ed. Engl 1989, 28, 626.
43. (e) Dobashi, A.; Motoyama, Y.; Kinoshita, K.; Hara, S. Anal. Chem. 1987, 59, 9.
44. (f) Tsai, W. I.; Hermann, K.; Hug, E.; Rohde, A. S.; Dreiding, A. S. Helv. Chim. Acta 1985, 68, 2238.
45. (g) Charles, E.; Gil-An, E. J. Chromatogr. 1984, 298, 516.
46. (h) Cundy, K. C.; Crooks, P. A. J. Chromatogr. 1983, 281, 17.
47. 3)], respectively.