Issue 3, 2016
From the journal:

Catalysis Science & Technology

Remarkable co-catalyst effects on the enantioselective hydrogenation of unfunctionalised enamines: both enantiomers of product from the same enantiomer of catalyst†

Sergey Tin,a   Tamara Fanjulb  and  Matthew L. Clarke*a  

* Corresponding authors

a School of Chemistry, University of St Andrews, EaStCHEM, St Andrews, Fife, UK
E-mail: mc28@st-andrews.ac.uk
Fax: +44 (0)1334 463808

b Chirotech Technology Centre, Dr. Reddy's Laboratories, Unit 410 Cambridge Science Park, Milton Road, Cambridge, CB4 0PE UK

Abstract

During studies on the enantioselective hydrogenation of unfunctionalised enamines, a very surprising switch in enantiopreference was observed; [((R,R)-Et-DUPHOS)-Rh(COD)]BF4 hydrogenates an enamine to give (R)-amine with up to 73% ee, but when iodine is added as a co-catalyst, the (S)-amine is formed with up to 61% ee. Mechanistic studies implicate a protonation-iminium ion reduction pathway.

Graphical abstract: Remarkable co-catalyst effects on the enantioselective hydrogenation of unfunctionalised enamines: both enantiomers of product from the same enantiomer of catalyst

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Article information

DOI
https://doi.org/10.1039/C5CY02051D
Article type
Communication
Submitted
27 Nov 2015
Accepted
07 Dec 2015
First published
09 Dec 2015

Catal. Sci. Technol., 2016,6, 677-680

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Remarkable co-catalyst effects on the enantioselective hydrogenation of unfunctionalised enamines: both enantiomers of product from the same enantiomer of catalyst

S. Tin, T. Fanjul and M. L. Clarke, Catal. Sci. Technol., 2016, 6, 677 DOI: 10.1039/C5CY02051D

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