Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine
AbstractIn this article we demonstrate how asymmetric total synthesis of (S)-rivastigmine has been achieved using direct asymmetric reductive amination as the key transformation in four steps. The route started with readily available and cheap m-hydroxyacetophenone, through esterification, asymmetric reductive amination, N-diphenylmethyl deprotection and reductive amination, to provide the final (S)-rivastigmine in 82% overall yield and 96% enantioselectivity. In the asymmetric reductive amination, catalysed by the iridium–phosphoramidite ligand complex and helped by some additives, the readily prepared 3-acetylphenyl ethyl(methyl)carbamate directly reductively coupled with diphenylmethanamine to yield the chiral amine product in 96% ee and 93% yield. View Full-Text
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Gao, G.; Du, S.; Yang, Y.; Lei, X.; Huang, H.; Chang, M. Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine. Molecules 2018, 23, 2207.
Gao G, Du S, Yang Y, Lei X, Huang H, Chang M. Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine. Molecules. 2018; 23(9):2207.Chicago/Turabian Style
Gao, Guorui; Du, Shaozhi; Yang, Yang; Lei, Xue; Huang, Haizhou; Chang, Mingxin. 2018. "Direct Asymmetric Reductive Amination for the Synthesis of (S)-Rivastigmine." Molecules 23, no. 9: 2207.
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