Asymmetric approaches to 2-hydroxymethylquinuclidine derivatives

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2795-2810

  Lygo, B ^a   Crosby, J ^b   Lowdon, T ^c   Wainwright, P G ^a  

^a UNIVERSITY OF SALFORD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c Hickson and Welch Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

QUINUCLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; EPOXIDATION; HYDROXYLATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033605309     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00050-2     Document Type: Article

References (32)

1. Lygo, B; Crosby, J; Lowdon, T.R; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 2343; Lygo, B; Wainwright, P.G, Tetrahedron Lett., 1997, 38, 8595; Lygo, B; Wainwright, P.G, Tetrahedron Lett., 1998, 39, 1599.
2. Lygo, B; Crosby, J; Lowdon, T.R; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 2343; Lygo, B; Wainwright, P.G, Tetrahedron Lett., 1997, 38, 8595; Lygo, B; Wainwright, P.G, Tetrahedron Lett., 1998, 39, 1599.
3. Lygo, B; Crosby, J; Lowdon, T.R; Wainwright, P.G. Tetrahedron Lett., 1997, 38, 2343; Lygo, B; Wainwright, P.G, Tetrahedron Lett., 1997, 38, 8595; Lygo, B; Wainwright, P.G, Tetrahedron Lett., 1998, 39, 1599.
4. Noyori, R. "Asymmetric Catalysis In Organic Synthesis", John Wiley and Sons, New York, 1994; "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993.
5. Noyori, R. "Asymmetric Catalysis In Organic Synthesis", John Wiley and Sons, New York, 1994; "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993.
6. Verporte, R. In "Monoterpene Indole Alkaloids", Saxton, J.E. (Ed.), 1994, John Wiley and Sons, New York, 1994, p647
7. Verporte, R; Schripsema, J; Van der Leer, T. In "The Alkaloids, Vol 14", Brossi, A (Ed.), Academic Press, San Diego, 1988, p331.
8. See: Ashwood, M.S; Gibson, A.W; Houghton, P.G; Humphrey, G.R; Roberts, D.C; Wright, H.B, J. Chem. Soc., Perkin Trans. I, 1995, 641 and references therein.
9. Sharpless, K.B; Amberg, W; Bennani, Y.L; Crispino, G.A; Hartung, J; Jeong, K-S; Kwong, H-L; Morikawa, K; Wang, Z-M; Xu, D; Zhang, X-L. J. Org. Chem., 1992, 57, 2768.
10. Reddy, K.L; Sharpless, K.B. J. Am. Chem. Soc., 1998, 120, 1207 and references therein.
11. Smaardijk, A.A; Wynberg, H, J. Org. Chem., 1987, 52, 135.
12. Simons, K.E; Ibbotson, A; Johnston, P; Plum, H; Wells, P.B, J. Cat., 1994, 150, 321.
13. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389. See also Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775 and references therein.
14. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389. See also Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775 and references therein.
15. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389. See also Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775 and references therein.
16. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389. See also Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775 and references therein.
17. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389. See also Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775 and references therein.
18. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389. See also Corey, E.J; Xu, F; Noe, M.C. J. Am. Chem. Soc., 1997, 119, 12414; Corey, E.J; Noe, M.C; Xu, F. Tetrahedron Lett., 1998, 39, 5347; Macdonald G; Alcaraz L; Lewis N.J; Taylor R.J.K. Tetrahedron Lett., 1998, 39, 5433; Arai, S; Oku, M; Miura, M; Shioiri, T. Synlett, 1998, 1201; O'Donnel, M.J; Delgado, F; Hostettler, C; Schwesinger, R. Tetrahedron Lett., 1998, 39, 8775 and references therein.
19. For previous synthetic approaches to racemic compounds of this type see: (a) Kolb, H.C; Andersson, P.G; Sharpless, K.B. J. Am. Chem. Soc., 1994, 116, 1278; (b) Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29; (c) Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646. For previous approaches to non-racemic compounds of this type see: (d) Pluim, H, Ph.D. Thesis, Rijksuniversiteit te Gröningen, 1982.
20. For previous synthetic approaches to racemic compounds of this type see: (a) Kolb, H.C; Andersson, P.G; Sharpless, K.B. J. Am. Chem. Soc., 1994, 116, 1278; (b) Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29; (c) Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646. For previous approaches to non-racemic compounds of this type see: (d) Pluim, H, Ph.D. Thesis, Rijksuniversiteit te Gröningen, 1982.
21. For previous synthetic approaches to racemic compounds of this type see: (a) Kolb, H.C; Andersson, P.G; Sharpless, K.B. J. Am. Chem. Soc., 1994, 116, 1278; (b) Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29; (c) Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646. For previous approaches to non-racemic compounds of this type see: (d) Pluim, H, Ph.D. Thesis, Rijksuniversiteit te Gröningen, 1982.
22. For previous synthetic approaches to racemic compounds of this type see: (a) Kolb, H.C; Andersson, P.G; Sharpless, K.B. J. Am. Chem. Soc., 1994, 116, 1278; (b) Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29; (c) Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646. For previous approaches to non-racemic compounds of this type see: (d) Pluim, H, Ph.D. Thesis, Rijksuniversiteit te Gröningen, 1982.
23. Aires-De-Sousa, J; Lobo, A.M; Prabhakar, S; Tetrahedron Lett., 1996, 37, 3183.
24. (a) Gao, Y; Hanson, R.M; Klunder, J.M; Ko, S.Y; Masamune, H; Sharpless, K.B. J. Am. Chem. Soc., 1987, 109, 5765; (b) Linker, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 2060.
25. (a) Gao, Y; Hanson, R.M; Klunder, J.M; Ko, S.Y; Masamune, H; Sharpless, K.B. J. Am. Chem. Soc., 1987, 109, 5765; (b) Linker, T. Angew. Chem. Int. Ed. Engl., 1997, 36, 2060.
26. Sharpless, K.B; Amberg, W; Bennani, Y.L; Crispino, G.A; Hartung, J; Jeong, K-S; Kwong, H-L; Morikawa, K; Wang, Z-M; Xu, D; Zhang, X-L. J. Org. Chem., 1992, 57, 2768.
27. Kolb, H.C; Sharpless, K.B. Tetrahedron, 1992, 48, 10515.
28. Gutzwiller, J; Uskokovi'c, M.R. J. Am. Chem. Soc., 1978, 100, 576; Adam, S. Tetrahedron, 1994, 50, 3327.
29. Gutzwiller, J; Uskokovi'c, M.R. J. Am. Chem. Soc., 1978, 100, 576; Adam, S. Tetrahedron, 1994, 50, 3327.
30. 1H nmr analysis of crude mixtures.
31. 1H chemical shifts of H-1 and H-2.
32. Perrin, D.D; Armarego, W.L.F. "Purification of Laboratory Chemicals", 3rd Ed., Pergamon Press, Oxford, 1988.