Stereoselective Access to Spiro-isoindolinone Scaffolds via Catalytic Asymmetric aza-Piancatelli Rearrangement

A chiral Brønsted acid catalyzed asymmetric aza-Piancatelli rearrangement of 3-furyl-3-hydroxyisoindolinones with anilines has been developed, enabling the divergent construction of chiral spiro-cyclopentenone-isoindolinones in high yields with excellent diastereo- and enantioselectivities even under a low catalyst loading of 0.5 mol%.

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Publication Details

Journal
Organic Letters
Published
2024-08-29
DOI
https://doi.org/10.1021/acs.orglett.4c02799
Citations
9
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
Field-Weighted Citation Impact
2.25

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article

Stereoselective Access to Spiro-isoindolinone Scaffolds via Catalytic Asymmetric aza-Piancatelli Rearrangement

Yunfei Cai, Yurong Tang, Ling Yu, Xukun Nie
9 citations
Organic Letters
Synthesis and pharmacology of benzodiazepine derivatives
2.25
article

Stereoselective Access to Spiro-isoindolinone Scaffolds via Catalytic Asymmetric aza-Piancatelli Rearrangement

Yunfei Cai, Yurong Tang, Ling Yu, Xukun Nie
article en
9 citations

Abstract

A chiral Brønsted acid catalyzed asymmetric aza-Piancatelli rearrangement of 3-furyl-3-hydroxyisoindolinones with anilines has been developed, enabling the divergent construction of chiral spiro-cyclopentenone-isoindolinones in high yields with excellent diastereo- and enantioselectivities even under a low catalyst loading of 0.5 mol%.

Organic LettersVol. 26(36)
Chongqing University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Chongqing, Venture and Innovation Support Program for Chongqing Overseas Returnees
Openalex Percentile: Top 12%
Synthesis and pharmacology of benzodiazepine derivatives
2.25
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