Citation: Long Jin, Jian Han, Dongmei Fang, Min Wang, Jian Liao. Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones[J]. Chinese Chemical Letters, ;2024, 35(6): 109212. doi: 10.1016/j.cclet.2023.109212 shu

Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones

Long Jin ^{a, c} ,
Jian Han ^b ,
Dongmei Fang ^a ,
Min Wang ^a ,
Jian Liao ^{a, c, *,}

a.
Natural Products Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China
b.
College of Chemical Engineering, Sichuan University, Chengdu 610065, China
c.
University of Chinese Academy of Sciences, Beijing 100049, China

jliao@cib.ac.cn

Received Date: 18 July 2023
Revised Date: 28 September 2023
Accepted Date: 12 October 2023
Available Online: 14 October 2023

Figures(6)

Ynones are important skeletons in bioactive molecules and valuable building blocks for organic synthesis, thus great efforts have been devoted to their preparation. While, introducing prochiral substrates to construct ynones bearing a chiral framework is unrealized to date. Herein, we reported the first example of Pd/SOP-catalyzed asymmetric carbonylative alkynylation via a non-classical carbonylative Sonogashira-type approach (acyl-Pd(Ⅱ) species generated from nucleophiles). By using cyclic diaryliodonium salts as prochiral substrates, various axial chiral ynones with good functional group tolerance (39 examples), satisfied yields (71%-96%) and excellent enantioselectivities (generally 94%-99% ee) were produced. Synthesis of bioactive compounds, scale-up experiment and useful transformations were also conducted to demonstrate the utility of this process.
- Pd-catalyzed,
- Axial chiral ynones,
- Cyclic diaryliodonium,
- High-valent palladium catalyzed,
- Asymmetric carbonyl alkynylation
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