Journal
TETRAHEDRON
Volume 68, Issue 37, Pages 7691-7694Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.06.031
Keywords
Rivastigmine; Transaminase; Biocatalysis; Asymmetric synthesis
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Funding
- Evonik Degussa GmbH
- BMBF (Germany)
- Austrian Science Fund (FWF) [W 901] Funding Source: researchfish
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(S)-Rivastigmine [(S)-1] was obtained via a four-step synthesis using an asymmetric enzymatic transamination protocol as the key step. An early introduction of the carbamate pharmacophore side chain avoided the use of protective group strategies and hence led to a considerable shortcut. This strategy required a novel omega-transaminase from Paracoccus denitrificans, which could transform the highly polar key substrate 3-acetylphenyl ethyl(methyl)carbamate (4) to the corresponding amine (S)-5 in 99% ee and >80% conversion. (C) 2012 Elsevier Ltd. All rights reserved.
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