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  Enantioselective reduction of α-dialkylamino ketones

Tomasz Kosmalski 1,  Marek Zaidlewicz 2

1. Nicolaus Copernicus University, Collegium Medicum, Department of Organic Chemistry, M. Skłodowska-Curie 9, Bydgoszcz 85-094, Poland
2. Nicolaus Copernicus University, Faculty of Chemistry (WChUMk), Gagarina 7, Toruń 87-100, Poland

Abstract
Abstract

     Catalytic hydrogenation has been widely applied to achieve asymmetric reductions of aryl-chloromethyl ketones1,2.

A highly selective and convenient method of asymmetric synthesis of β-N,N-dialkylamino alcohols has been developed by the transfer hydrogenation (ATH)3. The importance of this class of physiologically active compounds is increasing. Many of them are β-blockers and exhibite psychotropic activity. The reaction affords the corresponding β-N,N-dialkylamino alcohols with high enantioselectivity, 97-99%.


(-)-Macromerine, a natural alkaloid of the Coryphantha macromeris cactus, has been obtained by the transfer hydrogenation of α-N,N-dialkylamino ketone in the presence of Noyori's ruthenium catalyst with 98% ee.


1)    Hamada T., Torii T., Izawa K., Noyori R., Ikariya T., Org. Lett., 2002, 4, 4373.
2)    Tanis S. P., Evans B. R., Nieman J. A., Parker T. T., Taylor W. D., Haesley S. E.,  Herrington P. M., Perrault W. R., Hohler R. A., Dolak L. A., Hester M. R., Seest E. P.,  Tetrahedron: Asymmetry, 2006, 17, 2154.    
3)    T. Kosmalski, A. Wojtczak, M. Zaidlewicz.  „Asymmetric synthesis of α-dialkyloamino alcohols by transfer hydrogenation of α-amino ketones”.  Tetrahedron: Asymmetry, 2009, 20, 1138.
 

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Presentation: Oral at VII Multidyscyplinarna Konferencja Nauki o Leku, by Tomasz Kosmalski
See On-line Journal of VII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2010-03-31 13:40
Revised:   2010-04-02 14:23