Enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine

Tetrahedron Letters

Volumn 38, Issue 13, 1997, Pages 2343-2346

  Lygo, Barry ^a   Crosby, John ^b   Lowdon, Terence R ^c   Wainwright, Philip 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

CINCHONA ALKALOID; QUINUCLIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031592561     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00310-9     Document Type: Article

References (18)

1. 1. Verporte, R. In "Monoterpene Inaole Alkaloids", Saxton, J.E. (Ed.), 1994, John Wiley and Sons, New York, 1994, p647
2. 2. Verporte, R; Schripsema, J; Van der Leer, T. In "The Alkaloids, Vol 14", Brossi, A (Ed.), Academic Press, San Diego, 1988, p331.
3. 3. Noyori, R. "Asymmetric Catalysis In Organic Synthesis", John Wiley and Sons, New York, 1994.
4. 4. 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.
5. 5. 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.
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7. 7. Simons, K.E; Ibbotson, A; Johnston, P; Plum, H; Wells, P.B. J. Cat., 1994, 150, 321.
8. 8. O'Donnell, M.J. In "Catalytic Asymmetric Synthesis", Ojima, I (Ed.), VCH, Weinheim, 1993, p 389.
9. 9. Kolb, H.C; Andersson, P.G; Sharpless, K.B. J. Am. Chem. Soc., 1994, 116, 1278.
10. 10. For previous synthetic approaches to (±)-2-(α-hydroxybenzyl)quinuclidines see: Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646 (erythro and threo); Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29 (erythro). For synthesis and resolution of erythro-2-(α-hydroxybenzyl)quinuclidine see: Pluim, H. Ph.D. Thesis, Rijksuniversiteit Te, Groningen, 1982.
11. 10. For previous synthetic approaches to (±)-2-(α-hydroxybenzyl)quinuclidines see: Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646 (erythro and threo); Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29 (erythro). For synthesis and resolution of erythro-2-(α-hydroxybenzyl)quinuclidine see: Pluim, H. Ph.D. Thesis, Rijksuniversiteit Te, Groningen, 1982.
12. 10. For previous synthetic approaches to (±)-2-(α-hydroxybenzyl)quinuclidines see: Braschler, V; Grob, C.A; Kaiser, A. Helv. Chim. Acta, 1963, 46, 2646 (erythro and threo); Stotter, P.L; Friedman, M.D; Minter, D.E. J. Org. Chem., 1985, 50, 29 (erythro). For synthesis and resolution of erythro-2-(α-hydroxybenzyl)quinuclidine see: Pluim, H. Ph.D. Thesis, Rijksuniversiteit Te, Groningen, 1982.
13. 11. At the outset of this work piperidine-4-ethanol was commercially available from a variety of sources, however this is no longer the case. As a consequence we now prepare this material from 4-acetyl pyridine according to the following scheme: (equation presented)
14. 12. Kolb, H.C; Sharpless, K.B. Tetrahedron, 1992, 48, 10515.
15. 13. Baldwin, J.E. J. Chem. Soc., Chem. Commun., 1976, 734.
16. 14. Gutzwiller, J; Uskokovi'c, M.R. J. Am. Chem. Soc., 1978, 100, 576; Adam, S. Tetrahedron, 1994, 50, 3327.
17. 14. Gutzwiller, J; Uskokovi'c, M.R. J. Am. Chem. Soc., 1978, 100, 576; Adam, S. Tetrahedron, 1994, 50, 3327.
18. 15. The absolute stereochemistry of compounds (9) and (15) is tentatively assigned based on comparison of optical rotation with the corresponding Cinchona alkaloids. This assignment is also in agreement with the absolute stereochemistry anticipated from the asymmetric dihydroxylation.