Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones via a hydrogenation/isomerization cascade

Kun Wang; Saisai Niu; Weijun Tang; Dong Xue; Jianliang Xiao; Hongfeng Li; Chao Wang

doi:10.1039/D4CC00356J

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Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones via a hydrogenation/isomerization cascade†

Kun Wang,‡^ab Saisai Niu,‡^b Weijun Tang,

*^b Dong Xue,

^b Jianliang Xiao,^c Hongfeng Li^a and Chao Wang

*^b

Author affiliations

* Corresponding authors

^a Huzhou Key Laboratory of Green Energy Materials and Battery Cascade Utilization, School of Intelligent Manufacturing, Huzhou College, Huzhou, China

^b Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an 710062, China
E-mail: tangwj@snnu.edu.cn, c.wang@snnu.edu.cn

^c Department of Chemistry, University of Liverpool, Liverpool, UK

Abstract

Ru-catalyzed asymmetric hydrogenation of α-substituted α,β-unsaturated ketones has been developed for the enantioselective synthesis of chiral α-substituted secondary alcohols with high diastereo- and enantioselectivities (up to >99 : 1 dr, 98% ee). Mechanistic experiments suggest that the reaction proceeds via a Ru-catalyzed asymmetric hydrogenation of the C [double bond, length as m-dash] O bond in concert with a base-promoted allylic alcohol isomerization, and the final stereoselectivities were controlled by a DKR process during the asymmetric hydrogenation of the ketone intermediate.

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DOI: https://doi.org/10.1039/D4CC00356J
Article type: Communication
Submitted: 30 Jan 2024
Accepted: 19 Mar 2024
First published: 21 Mar 2024

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Chem. Commun., 2024,60, 4338-4341

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Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones via a hydrogenation/isomerization cascade

K. Wang, S. Niu, W. Tang, D. Xue, J. Xiao, H. Li and C. Wang, Chem. Commun., 2024, 60, 4338 DOI: 10.1039/D4CC00356J

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Chemical Communications

Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones via a hydrogenation/isomerization cascade†

Abstract

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Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones via a hydrogenation/isomerization cascade

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