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Issue 58, 2017
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Rhodium-catalyzed asymmetric hydrogenation of tetrasubstituted β-acetoxy-α-enamido esters and efficient synthesis of droxidopa

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Abstract

A rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted β-acetoxy-α-enamido esters was developed, giving chiral β-acetoxy-α-amido esters in high yields with excellent enantioselectivities (up to >99% ee). The products could be easily transformed to β-hydroxy-α-amino acid derivatives which are valuable chiral building blocks and a novel route for the synthesis of droxidopa was also developed.

Graphical abstract: Rhodium-catalyzed asymmetric hydrogenation of tetrasubstituted β-acetoxy-α-enamido esters and efficient synthesis of droxidopa

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Publication details

The article was received on 19 May 2017, accepted on 15 Jun 2017 and first published on 16 Jun 2017


Article type: Communication
DOI: 10.1039/C7CC03902F
Citation: Chem. Commun., 2017,53, 8136-8139
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    Rhodium-catalyzed asymmetric hydrogenation of tetrasubstituted β-acetoxy-α-enamido esters and efficient synthesis of droxidopa

    Y. Guan, M. Gao, X. Deng, H. Lv and X. Zhang, Chem. Commun., 2017, 53, 8136
    DOI: 10.1039/C7CC03902F

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