Synthesis and application of new β-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

Tetrahedron Asymmetry

Volumn 8, Issue 12, 1997, Pages 2007-2015

  Wilken, Jörg ^a   Kossenjans, Michael ^b   Gröger, Harald ^b   Martens, Jürgen ^b  

^a Arklow Co   (Ireland)

^b UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZALDEHYDE;

ALKYLATION; ARTICLE; CATALYSIS; CONFORMATION; DRUG STRUCTURE; INDUSTRIAL WASTE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030925001     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00201-2     Document Type: Article

References (23)

1. The compound (all-R)-1a is a non-recyclable, enantiomerically pure waste material which is obtained in the process of synthesizing the ACE-inhibitor ramipril by Hoechst AG: a) V. Teetz, R. Geiger, H. Gaul, Tetrahedron Lett. 1984, 25, 4479-4482;
2. b) H. Urbach, R. Henning, Heterocycles 1989, 28, 957-965.
3. Enantioselective borane reduction of ketones: a) J. Wilken, C. Thorey, H. Gröger, D. Haase, W. Saak, S. Pohl, J. Martens, Liebigs Ann/Recueil 1997, in print;
4. b) S. Wallbaum, J. Martens, Tetrahedron: Asymmetry 1991, 2, 1093-1096;
5. c) J. Wilken, J. Martens, Synth. Commun. 1996, 26, 4477-4485;
6. d) I. Reiners, J. Wilken, J. Martens, Tetrahedron: Asymmetry 1995,12, 3063-3070,
7. e) J. Wilken, J. Martens, Liebigs Ann./Recueil 1997, 563-571.
8. Enantioselective keto-enol tautomerization: S. J. Aboulhoda, S. Létinois, J. Wilken, I. Reiners, F. Hénin, J. Martens, J. Muzart, Tetrahedron: Asymmetry 1995, 6, 1865-1868.
9. Enantioselective addition of diethylzinc to aldehydes: a) K. Stingl, J. Martens, Liebigs Ann. 1994, 491-496;
10. b) J. Eilers, J. Wilken, J. Martens, Tetrahedron: Asymmetry 1996, 7, 2343-2357;
11. c) S. Wallbaum, J. Martens, Tetrahedron: Asymmetry 1993, 4, 637-649.
12. J. Wilken, Ph. D. thesis, Universität Oldenburg 1997.
13. M. Kossenjans, unpublished results, Universität Oldenburg, 1996. A general procedure for the preparation of related compounds is given in: J. Wilken, M. Kossenjans, W. Saak, D. Haase, S. Pohl, J. Martens, Liebigs Ann./Recueil 1997, 573-579.
14. M. Kossenjans, unpublished results, Universität Oldenburg, 1996. A general procedure for the preparation of related compounds is given in: J. Wilken, M. Kossenjans, W. Saak, D. Haase, S. Pohl, J. Martens, Liebigs Ann./Recueil 1997, 573-579.
15. S. Wallbaum, Ph. D. thesis, Universität Oldenburg, 1994.
16. For representative references about enantioselective dialkylzinc addition to aldehydes, see: a) M. Kitamura, S. Suga, K. Kawai, R. Noyori, J. Am. Chem. Soc. 1986, 108, 6071-6072;
17. b) M. Kitamura, S. Okada, S. Suga, R. Noyori, J. Am. Chem. Soc. 1989, 111, 4028-4036;
18. c) D. Seebach, A. K. Beck, B. Schmidt, Y. M. Wang, Tetrahedron 1994, 50, 4363-4384;
19. d) for a review, see: K. Soai, S. Niwa, Chem. Rev. 1992, 92, 833-856.
20. R. H. Richard, J. Kenyon, J. Chem. Soc. 1936, 128-129.
21. In general, the determination of optical purity is affected by a systematic error in the range of 2-4%, see: V. Schurig, in: Houben-Weyl, Methods of Organic Chemistry, Workbench-Edition E21, Vol. 1, Eds: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Thieme, Stuttgart, 1996, pp. 151-157.
22. K. Soai, A. Ookawa, T. Kaba, K. Ogawa, J. Am. Chem. Soc. 1987, 109, 7111-7115.
23. 13C-NMR spectroscopy.