Issue 7, 2018

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
16 Jan 2018
Accepted
24 Jan 2018
First published
24 Jan 2018

Org. Chem. Front., 2018,5, 1209-1212

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

G. Gu, T. Yang, J. Lu, J. Wen, L. Dang and X. Zhang, Org. Chem. Front., 2018, 5, 1209 DOI: 10.1039/C8QO00047F

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