Synthesis and application of C2-symmetrical bis-β-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

Tetrahedron Asymmetry

Volumn 10, Issue 22, 1999, Pages 4437-4445

  Wassmann, Suzanne ^a   Wilken, Jörg ^b   Martens, Jürgen ^c  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^b Riedel de Haën GmbH   (Germany)

^c UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZALDEHYDE; DIETHYLZINC; PYRROLE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONCENTRATION (PARAMETERS); ENANTIOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033370348     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00475-9     Document Type: Article

References (23)

1. The compound (all-R)-1 is a non-recyclable, enantiomerically pure waste material which is obtained in the process of synthesizing the ACE-inhibitor ramipril by Hoechst AG: (a) Teetz, V.; Geiger, R.; Gaul, H. Tetrahedron Lett. 1984, 25, 4479-4482. (b) Urbach, H.; Henning, R. Heterocycles 1989, 28, 957-965. The present paper is Part 15 of our series of publications on the utilization of industrial waste materials. For Part 14, see: loc. cit. 2f.
2. The compound (all-R)-1 is a non-recyclable, enantiomerically pure waste material which is obtained in the process of synthesizing the ACE-inhibitor ramipril by Hoechst AG: (a) Teetz, V.; Geiger, R.; Gaul, H. Tetrahedron Lett. 1984, 25, 4479-4482. (b) Urbach, H.; Henning, R. Heterocycles 1989, 28, 957-965. The present paper is Part 15 of our series of publications on the utilization of industrial waste materials. For Part 14, see: loc. cit. 2f.
3. Enantioselective addition of diethylzinc to aldehydes: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637-649. (b) Stingl, K.; Martens, J. Liebigs Ann. 1994, 491-496. Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 8, 2343-2357. Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 12, 2007-2015. (e) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 16, 2761-2771. (f) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
4. Enantioselective addition of diethylzinc to aldehydes: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637-649. (b) Stingl, K.; Martens, J. Liebigs Ann. 1994, 491-496. Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 8, 2343-2357. Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 12, 2007-2015. (e) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 16, 2761-2771. (f) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
5. Enantioselective addition of diethylzinc to aldehydes: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637-649. (b) Stingl, K.; Martens, J. Liebigs Ann. 1994, 491-496. Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 8, 2343-2357. Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 12, 2007-2015. (e) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 16, 2761-2771. (f) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
6. Enantioselective addition of diethylzinc to aldehydes: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637-649. (b) Stingl, K.; Martens, J. Liebigs Ann. 1994, 491-496. Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 8, 2343-2357. Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 12, 2007-2015. (e) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 16, 2761-2771. (f) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
7. Enantioselective addition of diethylzinc to aldehydes: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637-649. (b) Stingl, K.; Martens, J. Liebigs Ann. 1994, 491-496. Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 8, 2343-2357. Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 12, 2007-2015. (e) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 16, 2761-2771. (f) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
8. Enantioselective addition of diethylzinc to aldehydes: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1993, 4, 637-649. (b) Stingl, K.; Martens, J. Liebigs Ann. 1994, 491-496. Eilers, J.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1996, 8, 2343-2357. Wilken, J.; Kossenjans, M.; Gröger, H.; Martens, J. Tetrahedron: Asymmetry 1997, 12, 2007-2015. (e) Wilken, J.; Gröger, H.; Kossenjans, M.; Martens, J. Tetrahedron: Asymmetry 1997, 16, 2761-2771. (f) Kossenjans, M.; Soeberdt, M.; Wallbaum, S.; Harms, K.; Martens, J.; Aurich, H. G. J. Chem. Soc., Perkin Trans. 1 1999, 2353-2365.
9. Enantioselective borane reduction of ketones: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1991, 2, 1093-1096. (b) Wilken, J.; Martens, J. Synth. Commun. 1996, 26, 4477-4485. Wilken, J.; Martens, J. Liebigs Ann./Recueil 1997, 563-571. Wilken, J.; Thorey, C.; Gröger, H.; Haase, D.; Saak, W.; Pohl, S.; Martens. J. Liebigs Ann./Recueil 1997, 2133-2146.
10. Enantioselective borane reduction of ketones: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1991, 2, 1093-1096. (b) Wilken, J.; Martens, J. Synth. Commun. 1996, 26, 4477-4485. Wilken, J.; Martens, J. Liebigs Ann./Recueil 1997, 563-571. Wilken, J.; Thorey, C.; Gröger, H.; Haase, D.; Saak, W.; Pohl, S.; Martens. J. Liebigs Ann./Recueil 1997, 2133-2146.
11. Enantioselective borane reduction of ketones: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1991, 2, 1093-1096. (b) Wilken, J.; Martens, J. Synth. Commun. 1996, 26, 4477-4485. Wilken, J.; Martens, J. Liebigs Ann./Recueil 1997, 563-571. Wilken, J.; Thorey, C.; Gröger, H.; Haase, D.; Saak, W.; Pohl, S.; Martens. J. Liebigs Ann./Recueil 1997, 2133-2146.
12. Enantioselective borane reduction of ketones: (a) Wallbaum, S.; Martens, J. Tetrahedron: Asymmetry 1991, 2, 1093-1096. (b) Wilken, J.; Martens, J. Synth. Commun. 1996, 26, 4477-4485. Wilken, J.; Martens, J. Liebigs Ann./Recueil 1997, 563-571. Wilken, J.; Thorey, C.; Gröger, H.; Haase, D.; Saak, W.; Pohl, S.; Martens. J. Liebigs Ann./Recueil 1997, 2133-2146.
13. Kossenjans, M. Ph.D. thesis, Universität Oldenburg, 1999.
14. Enantioselective keto-enol tautomerization: (a) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 1865-1868. (b) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847-1850.
15. Enantioselective keto-enol tautomerization: (a) Aboulhoda, S. J.; Létinois, S.; Wilken, J.; Reiners, I.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1995, 6, 1865-1868. (b) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Hénin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847-1850.
16. For recent reviews on the enantioselective addition of dialkylzinc to aldehydes, see: (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Fitzpatrick, K.; Hulst, R.; Kellogg, R. Tetrahedron: Asymmetry 1995, 6, 1861.
17. For recent reviews on the enantioselective addition of dialkylzinc to aldehydes, see: (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Fitzpatrick, K.; Hulst, R.; Kellogg, R. Tetrahedron: Asymmetry 1995, 6, 1861.
18. For recent reviews on the enantioselective addition of dialkylzinc to aldehydes, see: (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. (c) Fitzpatrick, K.; Hulst, R.; Kellogg, R. Tetrahedron: Asymmetry 1995, 6, 1861.
19. For recent reviews on the enantioselective addition of dialkylzinc to aldehydes, see: (a) Noyori, R.; Kitamura, M. Angew. Chem. 1991, 103, 34; Angew. Chem., Int. Ed. Engl. 1991, 30, 49. (b) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833. Fitzpatrick, K.; Hulst, R.; Kellogg, R. Tetrahedron: Asymmetry 1995, 6, 1861.
20. Wallbaum, S. Ph.D. thesis, Universität Oldenburg, 1993.
21. Braun, M. Angew. Chem. 1996, 108, 565-568; Angew. Chem., Int. Ed. Engl. 1996, 35, 486-489.
22. Braun, M. Angew. Chem. 1996, 108, 565-568; Angew. Chem., Int. Ed. Engl. 1996, 35, 486-489.
23. Reiners, I.; Wilken, J.; Martens, J. Tetrahedron: Asymmetry 1995, 12, 3063-3070.