The absolute configuration of the (+)- and (-)-cis- and (+)- and (-)-trans-1-benzyl-4-hydroxypiperidine-3-methanols: An unusual application of the 1H-NMR-mosher method

Helvetica Chimica Acta

Volumn 92, Issue 1, 2009, Pages 14-28

  Clerc, Christian ^a   Matarazzo, Igor ^a   Rüedi, Peter ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATIONS; BENZENEACETIC ACIDS; BIOLOGICAL REDUCTIONS; DIASTEREO SELECTIVITIES; HIGH FIELDS; METHOXY; MIMETICS; MOSHER METHODS; STARTING COMPOUNDS; TITLE COMPOUNDS; TRIFLUOROMETHYL; X-RAY CRYSTALLOGRAPHIC ANALYSIS; YEAST REDUCTIONS;

ALCOHOLS; CARBOXYLATION; HYDROCARBONS; METHANOL; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PARAFFINS; YEAST;

ONTOLOGY;

METHANOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ENANTIOMER; FERMENTATION; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 59649130083     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200800270     Document Type: Article

References (40)

1. W. Ganci, E. J. M. Meier, F. Merckling, G. Przibille, U. Ringeisen, P. Rüedi, Helv. Chim. Acta 1997, 80, 421;
2. S. Furegati, W. Ganci, G. Przibille, P. Rüedi, Helv. Chim. Acta 1998, 81,1127.
3. S. Furegati, O. Zerbe, P. Rüedi, Chem.-Biol. Interact. 2005,157-158, 48.
4. M. J. Stockli, P. Riiedi, Helv. Chim. Acta 2007, 90, 2058.
5. S. Furegati, F. Gorla, A. Linden, P. Riiedi, Chem.-Biol. Interact. 2005, 157-158, 415.
6. S. Furegati, W. Ganci, F. Gorla, U. Ringeisen, P. Riedi, Helv. Chim. Acta 2004, 87, 2629.
7. C. Clerc, 'Synthese und Charakterisierung von enantiomerenreinen N-heterocyclischen Phosphadecalinen als Inhibitoren von Acetylcholinesterase', Ph.D. Thesis, University of Zurich, 2008.
8. J. A. Dale, D. L. Dull, H. S. Mosher, J. Org. Chem. 1969, 34, 2543.
9. G. R. Sullivan, J. A. Dale, H. S. Mosher, J. Org. Chem. 1973, 38, 2143.
10. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512.
11. I. Ohtani, T. Kusumi, Y. Kahman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092.
12. P. A. Lorenzetto, A. Strehler, P. Rüedi, Helv. Chim. Acta 2006, 89, 3023.
13. D. Seebach, S. Roggo, T. Maetzke, H. Braunschweiger, J. Cercus, M. Krieger, Helv. Chim. Acta 1987, 70, 1605.
14. I. Matarazzo, 'Der stereochemische Verlauf der Reduktion von 4-Oxopiperidin-3-carboxylaten mit Bäckerhefe', M.Sc. Thesis, University of Zurich, 2008.
15. D. Seebach, S. Roggo, J. Zimmermann, 'Stereochemistry of Organic and Bioorganic Transformations', Workshop Conferences, Hoechst, Vol. 17, Eds. W. Bartmann and K. B. Sharpless, VCH-Verlagsgesellschaft Weinheim, 1987.
16. C. J. Shi, B. Zhou, A. S. Gopalan, W. R. Shieh, F. Van Middlesworth, in 'Selectivity - a Goal for Synthetic Efficiency', Workshop Conferences, Hoechst, Vol. 14, Eds. W. Bartmann and B. M. Trost, Verlag Chemie, Weinheim, 1983.
17. J. C. Shi, C.-S. Chen, Angew. Chem. 1984, 96, 556
18. R. Csuk, B. Glänzer, Chem. Rev. 1991, 91, 49.
19. C.-H. Wong, G. Whitesides, 'Enzymes in Synthetic Organic Chemistry', Pergamon, Oxford, 1995, p. 139.
20. H. Ripperger, K. Schreiber, Ber. Dtsch. Chem. Ges. 1969, 102, 2864.
21. G. Bettoni, E. Duranti, V. Tortorella, Gazz. Chim. Ital. 1972, 102, 189.
22. D. W. Knight, N. Lewis, A. C. Share, D. Haigh, Tetrahedron: Asymmetry 1993, 4, 625.
23. D. W. Knight, N. Lewis, A. C. Share, D. Haigh, J. Chem. Soc., Perkin Trans. 1 1998, 3673.
24. E. Brygesesn, J. Nielsen, M. Willert, M. Bols, Tetrahedron Lett. 1997, 32, 5697.
25. M. Willert, M. Bols, Acta Chem. Scand. 1998, 52, 461.
26. X. Liang, A. Lohse, M. Bols, J. Org. Chem. 2000, 65, 7432.
27. M. Roberti, R. Rondanin, R. Ferroni, R. Barucchello, F. P. Invidiata, V. Andrisano, C. Bertucci, V. Bertolasi, S. Grimaudo, M. Tolomeo, D. Simoni, Tetrahedron: Asymmetry 2000,11, 4397.
28. M. Solymár, E. Forró, F. Fiilop, Tetrahedron: Asymmetry 2004,15, 3281.
29. R. W. Hoffman, Chem. Rev. 1989, 89, 1841.
30. A. Jourdant, J. Zhu, Tetrahedron Lett. 2000, 41, 7033.
31. M. Wächter, P. Rüedi, in preparation.
32. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
33. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., and R. M. Sweet, Academic Press, New York, 1997, pp. 307 - 326.
34. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, J. Appl. Crystallogr. 1994, 27, 435.
35. E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, pp. 477-486.
36. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
37. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
38. D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.6.8, pp. 219-222.
39. D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.4.3, pp. 200-206.
40. G. M. Sheldrick, 'SHELXL97, Program for the Refinement of Crystal Structures', University of Göttingen, Germany, 1997.