An efficient enantioselective preparation of (S,S)-1,2-bis(1-hydroxyalkyl)benzene

Chemistry Letters

Volumn , Issue 11, 2001, Pages 1110-1111

  Asami, Masatoshi ^a   Wada, Masaaki ^a   Furuya, Sanae ^a  

^a YOKOHAMA NATIONAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035541186     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2001.1110     Document Type: Article

References (25)

1. 2 symmetry and asymmetric induction, see J. K. Whitesell, Chem. Rev., 89, 1581 (1989).
2. For example, R. A. Johnson, K. B. Sharpless, in "Catalytic Asymmetric Synthesis," ed. by I. Ojima, VCH Publishers, New York (1993), p 103; D. Seebach and B. Weber, Tetrahedron, 50, 7473 (1994); J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, and N. J. Taylor, Tetrahedron: Asymmetry, 6, 409 (1995); K. Yamaguchi, T. Sugimura, F. Nishida, and A. Tai, Tetrahedron Lett., 39, 4521 (1998); H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 122, 8180 (2000).
3. For example, R. A. Johnson, K. B. Sharpless, in "Catalytic Asymmetric Synthesis," ed. by I. Ojima, VCH Publishers, New York (1993), p 103; D. Seebach and B. Weber, Tetrahedron, 50, 7473 (1994); J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, and N. J. Taylor, Tetrahedron: Asymmetry, 6, 409 (1995); K. Yamaguchi, T. Sugimura, F. Nishida, and A. Tai, Tetrahedron Lett., 39, 4521 (1998); H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 122, 8180 (2000).
4. For example, R. A. Johnson, K. B. Sharpless, in "Catalytic Asymmetric Synthesis," ed. by I. Ojima, VCH Publishers, New York (1993), p 103; D. Seebach and B. Weber, Tetrahedron, 50, 7473 (1994); J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, and N. J. Taylor, Tetrahedron: Asymmetry, 6, 409 (1995); K. Yamaguchi, T. Sugimura, F. Nishida, and A. Tai, Tetrahedron Lett., 39, 4521 (1998); H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 122, 8180 (2000).
5. For example, R. A. Johnson, K. B. Sharpless, in "Catalytic Asymmetric Synthesis," ed. by I. Ojima, VCH Publishers, New York (1993), p 103; D. Seebach and B. Weber, Tetrahedron, 50, 7473 (1994); J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, and N. J. Taylor, Tetrahedron: Asymmetry, 6, 409 (1995); K. Yamaguchi, T. Sugimura, F. Nishida, and A. Tai, Tetrahedron Lett., 39, 4521 (1998); H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 122, 8180 (2000).
6. For example, R. A. Johnson, K. B. Sharpless, in "Catalytic Asymmetric Synthesis," ed. by I. Ojima, VCH Publishers, New York (1993), p 103; D. Seebach and B. Weber, Tetrahedron, 50, 7473 (1994); J. M. Chong, I. S. Clarke, I. Koch, P. C. Olbach, and N. J. Taylor, Tetrahedron: Asymmetry, 6, 409 (1995); K. Yamaguchi, T. Sugimura, F. Nishida, and A. Tai, Tetrahedron Lett., 39, 4521 (1998); H. Ishitani, M. Ueno, and S. Kobayashi, J. Am. Chem. Soc., 122, 8180 (2000).
7. H. C. Kolb, M. S. VanNieuwenhze, and K. B. Sharpless, Chem. Rev., 94, 2483 (1994).
8. M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, and R. Noyori, J. Am. Chem. Soc., 110, 629 (1988); G. J. Quallich, K. N. Keavey, and T. M. Woodall, Tetrahedron Lett., 36, 4729 (1995).
9. M. Kitamura, T. Ohkuma, S. Inoue, N. Sayo, H. Kumobayashi, S. Akutagawa, T. Ohta, H. Takaya, and R. Noyori, J. Am. Chem. Soc., 110, 629 (1988); G. J. Quallich, K. N. Keavey, and T. M. Woodall, Tetrahedron Lett., 36, 4729 (1995).
10. P. V. Ramachandran, G.-M. Chen, and H. C. Brown, Tetrahedron Lett., 38, 2417 (1997).
11. K. Soai, H. Hori, and M. Kawahara, J. Chem. Soc., Chem. Commun., 1992, 106.
12. a) M. Watanabe, N. Hashimoto, S. Araki, and Y. Butsugan, J. Org. Chem., 57, 742 (1992).
13. b) K. Soai, Y. Inoue, T. Takahashi, and T. Shibata, Tetrahedron, 52, 13355 (1996).
14. X. Zhang, U. S. Patent 5767276 (1998); Chem. Abstr., 129, 81855q (1998).
15. X. Zhang, U. S. Patent 5767276 (1998); Chem. Abstr., 129, 81855q (1998).
16. P. V. Ramachandran, G.-M. Chen, Z.-H. Lu, and H. C. Brown, Tetrahedron Lett., 37, 3795 (1996).
17. M. Asami, H. Watanabe, K. Honda, and S. Inoue, Tetrahedron: Asymmetry, 9, 4165 (1998).
18. The ee value was determined by HPLC using Daicel Chiralcel OB and the absolute configuration was assigned to be S as (S,S)-7 was obtained afterwards.
19. 13C NMR, IR) were obtained for these compounds.
20. R. Johansson and B. Samuelson, J. Chem. Soc., Perkin Trans. 1, 1984, 2371.
21. 7b
22. 3)) was determined to be 86% by HPLC using Daicel Chiralcel OB and the absolute configuration of (S)-9 was established by comparison of the specific rotation with reported value; S. Sato, H. Watanabe, and M. Asami, Tetrahedron: Asymmetry, 11, 4329 (2000).
23. The ee value was estimated to be >99% as only one enantiomer was detected by HPLC using Daicel Chiralcel OD-H. The absolute configuration was assigned to be S,S as the chiral center created in the first reaction was S.
24. I. Fleming, I. T. Morgan, and A. K. Sarkar, J. Chem. Soc., Perkin Trans. 1, 1998, 2749.
25. Y. Yokoyama, T. Okuyama, Y. Yokoyama, and M. Asami, Chem. Lett., 2001, 1112.