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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

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Sergey Tin, Tamara Fanjul, Matthew L. Clarke

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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.
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Original languageEnglish
Pages (from-to)677-680
Number of pages4
JournalCatalysis Science & Technology
Volume6
Issue number3
Early online date9 Dec 2015
DOIs
Publication statusPublished - 7 Feb 2016

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