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

Sergey Tin; Tamara Fanjul; Matthew L. Clarke

doi:10.1039/C5CY02051D

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

Sergey Tin, Tamara Fanjul, Matthew L. Clarke

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	677-680
Number of pages	4
Journal	Catalysis Science & Technology
Volume	6
Issue number	3
Early online date	9 Dec 2015
DOIs	https://doi.org/10.1039/C5CY02051D
Publication status	Published - 7 Feb 2016

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© 2016 the Authors. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1039/C5CY02051D
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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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AB - 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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Remarkable co-catalyst effects on the enantioselective hydrogenation of unfunctionalised enamines: both enantiomers of product from the same enantiomer of catalyst

Abstract

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