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Open AccessArticle

Multi-Catalytic Route for the Synthesis of (S)-Tembamide

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Institute for Biochemistry, Biotechnology and Bioinformatics, Technische Universität Braunschweig, Spielmannstr. 7, 38106 Braunschweig, Germany
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Viazym B.V., Molengraaffsingel 10, 2629, JD Delft, The Netherlands
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Institute for Inorganic and Analytical Chemistry, Technische Universität Braunschweig, Hagenring 30, 38106 Braunschweig, Germany
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Department of Biotechnology, Delft University of Technology, Van der Maasweg 9, 2629 HZ Delft, The Netherlands
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Author to whom correspondence should be addressed.
Catalysts 2019, 9(10), 822; https://doi.org/10.3390/catal9100822
Received: 6 September 2019 / Revised: 24 September 2019 / Accepted: 24 September 2019 / Published: 29 September 2019
Enantiopure β-amino alcohols constitute one of the most significant building blocks for the synthesis of active pharmaceutical ingredients. Despite the availability of a range of chiral β-amino alcohols from a chiral pool, there is a growing demand for new enantioselective synthetic routes to vicinal amino alcohols and their derivatives. In the present study, an asymmetric 2-step catalytic route that converts 4-anisaldehyde into a β-amino alcohol derivative, (S)-tembamide, with excellent enantiopurity (98% enantiomeric excess) has been developed. The recently published initial step consists in a concurrent biocatalytic cascade for the synthesis of (S)-4-methoxymandelonitrile benzoate. The O-benzoyl cyanohydrin is then converted to (S)-tembamide in a hydrogenation reaction catalyzed by Raney Ni. To achieve hydrogenation of the nitrile moiety with highest chemoselectivity and enantioretention, various parameters such as nature of the catalyst, reaction temperature and hydrogen pressure were studied. The reported strategy might be transferrable to the synthesis of other N-acyl-β-amino alcohols. View Full-Text
Keywords: enantioselectivity; chemoenzymatic cascade; hydroxynitrile lyase; lipase; raney ni; hydrocyanation; transesterification; catalytic hydrogenation; nitrile reduction; tembamide enantioselectivity; chemoenzymatic cascade; hydroxynitrile lyase; lipase; raney ni; hydrocyanation; transesterification; catalytic hydrogenation; nitrile reduction; tembamide
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MDPI and ACS Style

Leemans, L.; Walter, M.D.; Hollmann, F.; Schallmey, A.; van Langen, L.M. Multi-Catalytic Route for the Synthesis of (S)-Tembamide. Catalysts 2019, 9, 822.

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