Rhodium-catalyzed asymmetric hydrogenation of tetrasubstituted beta-acetoxy-alpha-enamido esters and efficient synthesis of droxidopa

A rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted beta-acetoxy-alpha-enamido esters was developed, giving chiral beta-acetoxy-alpha-amido esters in high yields with excellent enantio-selectivities (up to >99% ee). The products could be easily transformed to beta-hydroxy...

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Published inChemical communications (Cambridge, England) Vol. 53; no. 58; pp. 8136 - 8139
Main Authors Guan, Yu-Qing, Gao, Min, Deng, Xu, Lv, Hui, Zhang, Xumu
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 18.07.2017
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
HIGHLY ENANTIOSELECTIVE HYDROGENATION
LIGANDS
AMINO-ACIDS
STEREODIVERGENT SYNTHESIS
HYDROCHLORIDES
OLEFINS
IRIDIUM COMPLEX
D-THREONINE
DYNAMIC KINETIC RESOLUTION
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Summary:A rhodium-catalyzed asymmetric hydrogenation of challenging tetrasubstituted beta-acetoxy-alpha-enamido esters was developed, giving chiral beta-acetoxy-alpha-amido esters in high yields with excellent enantio-selectivities (up to >99% ee). The products could be easily transformed to beta-hydroxy-alpha-amino acid derivatives which are valuable chiral building blocks and a novel route for the synthesis of droxidopa was also developed.
Bibliography:ObjectType-Article-1
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ISSN:1359-7345
1364-548X
DOI:10.1039/c7cc03902f