Accessing Furan-2(5 <i>H</i> )-one-Substituted Cyclic Ketones via Rh-Catalyzed Carbene/Alkyne Metathesis-Triggered Semipinacol Rearrangement

In this work, we developed an efficient and practical method to construct diverse furan-2(5<i>H</i>)-one-substituted cyclic ketones. This strategy enables ring expansion via a carbene/alkyne metathesis-semipinacol rearrangement cascade, efficiently affording various functionalized products under mild conditions with a broad substrate scope. Moreover, a catalyst loading of only 0.1 mol % was sufficient to drive the reaction efficiently. Significantly, the method also allows for structural modifications of structurally complex natural products.

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Publication Details

Journal
Organic Letters
Published
2025-10-28
DOI
https://doi.org/10.1021/acs.orglett.5c03862
Primary Topic
Synthetic Organic Chemistry Methods
Type
article
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article

Accessing Furan-2(5 H )-one-Substituted Cyclic Ketones via Rh-Catalyzed Carbene/Alkyne Metathesis-Triggered Semipinacol Rearrangement

Yanting Che, Hejiang Luo, Guowei Yao, Rong‐Tao Li
Organic Letters
Synthetic Organic Chemistry Methods
article

Accessing Furan-2(5 H )-one-Substituted Cyclic Ketones via Rh-Catalyzed Carbene/Alkyne Metathesis-Triggered Semipinacol Rearrangement

Yanting Che, Hejiang Luo, Guowei Yao, Rong‐Tao Li
article en

Abstract

In this work, we developed an efficient and practical method to construct diverse furan-2(5<i>H</i>)-one-substituted cyclic ketones. This strategy enables ring expansion via a carbene/alkyne metathesis-semipinacol rearrangement cascade, efficiently affording various functionalized products under mild conditions with a broad substrate scope. Moreover, a catalyst loading of only 0.1 mol % was sufficient to drive the reaction efficiently. Significantly, the method also allows for structural modifications of structurally complex natural products.

Organic LettersVol. 27(44)
Kunming University of Science and Technology (CN)
Openalex Percentile: Top 76%
Synthetic Organic Chemistry Methods
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