Photoexcited Copper-Catalyzed Intramolecular [2+2] Cycloaddition To Construct Bicyclo[3.2.0]heptanes

The bicyclo[3.2.0]heptane scaffold is frequently found in a wide range of bioactive molecules and plays a pivotal role in constructing key modules of these compounds. In this study, we present a strategy for the synthesis of bicyclo[3.2.0]heptanes using a copper/BINAP complex to facilitate an intramolecular [2+2] cycloaddition under visible light irradiation. This methodology offers several advantages, including the use of a cost-effective copper catalyst and the ability to achieve high yields (up to 98%) and diastereoselectivity (>20:1 dr). Our approach provides an efficient strategy for constructing the bicyclo[3.2.0]heptane framework.

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Publication Details

Journal
Organic Letters
Published
2025-05-08
DOI
https://doi.org/10.1021/acs.orglett.5c01331
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
2.81

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article

Photoexcited Copper-Catalyzed Intramolecular [2+2] Cycloaddition To Construct Bicyclo[3.2.0]heptanes

Shouyun Yu, Hongling Xie
3 citations
Organic Letters
Radical Photochemical Reactions
2.81
article

Photoexcited Copper-Catalyzed Intramolecular [2+2] Cycloaddition To Construct Bicyclo[3.2.0]heptanes

Shouyun Yu, Hongling Xie
article en
3 citations

Abstract

The bicyclo[3.2.0]heptane scaffold is frequently found in a wide range of bioactive molecules and plays a pivotal role in constructing key modules of these compounds. In this study, we present a strategy for the synthesis of bicyclo[3.2.0]heptanes using a copper/BINAP complex to facilitate an intramolecular [2+2] cycloaddition under visible light irradiation. This methodology offers several advantages, including the use of a cost-effective copper catalyst and the ability to achieve high yields (up to 98%) and diastereoselectivity (>20:1 dr). Our approach provides an efficient strategy for constructing the bicyclo[3.2.0]heptane framework.

Organic LettersVol. 27(20)
Nanjing University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 11%
Radical Photochemical Reactions
2.81
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