Highly Regio- and Enantioselective Hydrogenation of Conjugated α‑Substituted Dienoic Acids
journal contributionposted 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.