Organocatalytic <i>syn</i> -Selective [3 + 2]/[4 + 2] Annulations of ( <i>E</i> )-Pyrazoloneyldiene Oxindole

H-Bonding organocatalysis enables highly <i>syn</i>-diastereo- and enantioselective [3 + 2]/[4 + 2] annulations of (<i>E</i>)-pyrazoloneyldiene oxindoles with γ/δ-hydroxyenones, furnishing the bispirotetrahydrofuran/bispirotetrahydropyran derivatives bearing vicinal quaternary centers. The reaction tolerates diverse substitution patterns to give up to 88% yield, >20:1 dr, and 99% ee. Control experiments and density functional theory were used to elucidate the role of the hydrogen-bond donor in <i>syn</i>-selective diastereocontrol.

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Publication Details

Journal
Organic Letters
Published
2025-10-22
DOI
https://doi.org/10.1021/acs.orglett.5c03738
Citations
1
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.94
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article

Organocatalytic syn -Selective [3 + 2]/[4 + 2] Annulations of ( E )-Pyrazoloneyldiene Oxindole

Yuzhen Chen, Xiaodong Han, Weihong Liang, Huicai Huang et al.
1 citations
Organic Letters
Asymmetric Synthesis and Catalysis
0.94
article

Organocatalytic syn -Selective [3 + 2]/[4 + 2] Annulations of ( E )-Pyrazoloneyldiene Oxindole

Yuzhen Chen, Xiaodong Han, Weihong Liang, Huicai Huang, Jialiang Qin, Bo Liu, Wenhong Suo
article en
1 citations

Abstract

H-Bonding organocatalysis enables highly <i>syn</i>-diastereo- and enantioselective [3 + 2]/[4 + 2] annulations of (<i>E</i>)-pyrazoloneyldiene oxindoles with γ/δ-hydroxyenones, furnishing the bispirotetrahydrofuran/bispirotetrahydropyran derivatives bearing vicinal quaternary centers. The reaction tolerates diverse substitution patterns to give up to 88% yield, >20:1 dr, and 99% ee. Control experiments and density functional theory were used to elucidate the role of the hydrogen-bond donor in <i>syn</i>-selective diastereocontrol.

Organic LettersVol. 27(43)
Guangzhou University of Chinese Medicine (CN), Ministry of Education of the People's Republic of China (CN), Sun Yat-sen University (CN), State Administration of Traditional Chinese Medicine of the People's Republic of China (CN), Guangdong Provincial Hospital of Traditional Chinese Medicine (CN), Shenzhen University Health Science Center (CN), Southern Medical University (CN)
Openalex Percentile: Top 20%
Asymmetric Synthesis and Catalysis
0.94
DOISourceOpenAlex
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Organocatalytic <i>syn</i> -Selective [3 + 2]/[4 + 2] Annulations of ( <i>E</i> )-Pyrazoloneyldiene Oxindole — Yuzhen Chen, Xiaodong Han, et al. · Organic Letters (2025) | TGRS Research Map | TGRS