American Chemical Society
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Highly Regio- and Enantioselective Hydrogenation of Conjugated α‑Substituted Dienoic Acids

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journal contribution
posted on 2020-03-27, 11:34 authored by Xian Liu, Song Liu, Quanjun Wang, Gang Zhou, Lin Yao, Qin Ouyang, Ru Jiang, Yu Lan, Weiping Chen
Highly regio- and enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer–Rh complex, providing a straightforward method for the synthesis of chiral α-substituted γ,δ-unsaturated acids. DFT calculations revealed N+H–O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh­(III) center would facilitate the reductive elimination process. This hydrogenation provided a gram-scale synthesis of the precursor of sacubitril.