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Ru-catalyzed asymmetric hydrogenation of α,β-unsaturated ketones via a hydrogenation/isomerization cascade. 2024
Kun Wang, and
Saisai Niu, and
Weijun Tang, and
Dong Xue, and
Jianliang Xiao, and
Hongfeng Li, and
Chao Wang
Huzhou Key Laboratory of Green Energy Materials and Battery Cascade Utilization, School of Intelligent Manufacturing, Huzhou College, Huzhou, 313000, China.
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 CO 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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