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Download fileHighly Regio- and Enantioselective Hydrogenation of Conjugated α‑Substituted Dienoic Acids
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 ChenHighly 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.