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Asymmetric Transfer
Hydrogenation of Acyclic 1,4-Diketones
for the Synthesis of Diversified Cyclic Products via Double Dynamic
Kinetic Resolution
Chao Xu (201376)
Shouang Lan (5797070)
Yunyun Jiao (25135680)
Xiang Lei (1740661)
Chunyun Jiang (12357358)
Lili Zhao (442802)
Shengyu Huang (6431606)
Siyu Shi (1462726)
Jinggong Liu (1528981)
Shuang Yang (64650)
Qi Zhang (28502)
Xinqiang Fang (1904908)
Biophysics
Biochemistry
Microbiology
Molecular Biology
Biotechnology
Chemical Sciences not elsewhere classified
Ecology
Biological Sciences not elsewhere classified
Information Systems not elsewhere classified
Computational Biology
five bioactive compounds
density functional theory
combined experimental studies
asymmetric transfer hydrogenation
active molecular families
access enantioenriched substances
acyclic racemic 1
converting acyclic substrates
acyclic 1
withdrawing groups
type neolignane
three categories
tetrahydrofurans
synthetic value
reaction conditions
r </
prunellanate b
powerful strategy
mechanistic insights
full article
four types
e </
>, 8
>)-( 7
7 ′<
Asymmetric transfer hydrogenation (ATH) serves as a powerful
strategy
to access enantioenriched substances; however, constructing diversified
molecular skeletons and converting acyclic substrates into cyclic
products via ATH remain challenging. In this full article, we report
on the selective ATH of acyclic racemic 1,4-diketones. By modulating
the electron-withdrawing groups (EWGs) on the substrates and tuning
the reaction conditions, four types of cyclic productsincluding
dihydrofurans, γ-lactones, tetrahydrofuranols, and tetrahydrofuransare
obtained through a double dynamic kinetic resolution (DKR) process.
Moreover, the synthetic value of this method has been demonstrated
by the synthesis of five bioactive compounds, i.e., megacerotonic
acid, (7′<i>E</i>)-(7<i>R</i>,8<i>R</i>)-salvianolic acid V, prunellanate B, calyxolane A, and
a magnosalicin-type neolignane, which fall into three categories of
active molecular families. Mechanistic insights are further elucidated
through combined experimental studies and density functional theory
(DFT) calculations.
2026-09-29T00:00:00Z
Text
Journal contribution
10.1021/jacs.6c17816.s001
https://figshare.com/articles/journal_contribution/Asymmetric_Transfer_Hydrogenation_of_Acyclic_1_4-Diketones_for_the_Synthesis_of_Diversified_Cyclic_Products_via_Double_Dynamic_Kinetic_Resolution/34021575
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