Diastereo- and enantioselective synthesis of cis-2- hydroxycyclohexanamine and corresponding ethers by asymmetric reductive amination

Tetrahedron Asymmetry

Volumn 8, Issue 20, 1997, Pages 3457-3466

  Lauktien, Gerhard ^a   Volk, Franz J ^a   Frahm, August W ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOHEXYLAMINE DERIVATIVE;

AMINATION; ARTICLE; CONFORMATION; DIASTEREOISOMER; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030697230     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00456-4     Document Type: Article

References (30)

1. Bradley, J. Physiol. 1966, 183(3), 658.
2. Overberger, C. G.; Marullo, N. P.; Hiskey, R. G. J. Am. Chem. Soc. 1961, 83, 1374.
3. (a) Weinges, K.; Gries, K.; Stemmle, B.; Schrank, W. Chem. Ber. 1977, 110, 2098.
4. (b) Stout, D. M.; Black, A. L.; Matier, W. L. J. Org. Chem. 1983, 48, 5369.
5. (c) Bringmann, G.; Geisler, J. P. Synthesis, 1989, 608.
6. Knupp, G.; Frahm, A. W. Chem. Ber. 1984, 117, 2076. Knupp, G. PhD Thesis, Bonn, 1982.
7. Knupp, G.; Frahm, A. W. Chem. Ber. 1984, 117, 2076. Knupp, G. PhD Thesis, Bonn, 1982.
8. Wiehl, W.; Frahm, A. W. Chem. Ber. 1986, 119, 2668. Wiehl, W. PhD Thesis, Bonn, 1985.
9. Wiehl, W.; Frahm, A. W. Chem. Ber. 1986, 119, 2668. Wiehl, W. PhD Thesis, Bonn, 1985.
10. Omar, F.; Frahm, A. W. Arch. Pharm. 1989, 322, 461.
11. Nachtsheim, C. M.; Frahm, A. W. Arch. Pharm. 1989, 322, 199.
12. Williamson, K. L.; Keller, R. T.; Fonken, G. S.; Szmuszkovicz, J.; Johnson, W. S. J. Org. Chem. 1962, 27, 1613.
13. Mousseron, M.; Jacquier, R. Can. J. Chem. 1976, 54, 2759.
14. Newmann, M. S.; Farbman, M. S. Org. Synth. Coll. Vol. III, 1945, 188.
15. (a) Bartlett, P.; Woods, G. J. Am. Chem. Soc. 1940, 62, 2933.
16. (b) Mayer, D. in Houben-Weyl, Methoden der organischen Chemie, 4.Aufl., 1977, Bd.7/2c, 2174.
17. Dürbeck, H. W.; Frischkorn, C.; Hilpert, K. Tetrahedron, 1971, 27, 2927.
18. Bergmann, M.; Gierth, M. Liebigs Ann.Chem. 1926, 48, 448.
19. Mayer, D. in Houben-Weyl, Methoden der organischen Chemie, 4.Aufl., 1977, Bd.7/2c, 2232.
20. Sheenan, J. C.; O'Neill, R. C.; White, M. A. J. Am. Chem. Soc. 1950, 72, 3376.
21. Kosolapoff, G. M. CA, 1964, 61, 1770g.
22. Will be published in a forthcoming paper.
23. Knupp, G.; Frahm, A. W. Arch. Pharm. 1985, 318, 250.
24. Liem, L. K.; Frahm, A. W. Arch. Pharm. 1991, 324, 335.
25. Mayer, D. in Houben-Weyl, Methoden der organische Chemie, 4.Aufl., 1977, Bd.7/2c, 2261.
26. Nishimura, S.; Uramoto, M.; Watanabe, T. Bull. Chem. Soc. Japan 1972, 45, 215.
27. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
28. Verbit, L; Price, H. C. J. Am. Chem. Soc. 1972, 94, 5143.
29. Unpublished results.
30. Lauktien, G. PhD Thesis, Bonn, 1990.