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Iridium/f-ampha-catalyzed asymmetric hydrogenation of aromatic α-keto esters

Authors :
Jiaxiang Lu
Guoxian Gu
Xumu Zhang
Jialin Wen
Tilong Yang
Li Dang
Source :
Organic Chemistry Frontiers. 5:1209-1212
Publication Year :
2018
Publisher :
Royal Society of Chemistry (RSC), 2018.

Abstract

We herein report an iridium/f-ampha catalytic system for the asymmetric hydrogenation of aromatic α-keto esters. This method was demonstrated to be efficient in preparing chiral mandelate esters with up to >99% conversion and up to 97% ee. DFT calculations revealed that a quadruple Na+–O ionic interaction is formed to stabilize the transition state. The (S)-isomeric product was favored due to steric hindrance.

Details

ISSN :
20524129
Volume :
5
Database :
OpenAIRE
Journal :
Organic Chemistry Frontiers
Accession number :
edsair.doi...........c991ccee3b9bb979e6ab78c6a4bf5302
Full Text :
https://doi.org/10.1039/c8qo00047f