Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks

Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to a diverse and functionalized array of cyclobutene frameworks adorned with a quaternary carbon center. This approach broadens the synthetic repertoire of 2-alkynylnaphthols with alkenes, offering a versatile platform for the construction of complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates a wide substrate scope and an impressive functional group tolerance, yielding products with high efficiency, up to 97% yield, and excellent enantiomeric excess of up to 97%. The simplicity of scaling up this process, coupled with the ease of converting these cyclobutene frameworks into a variety of substituted products, significantly enhances the synthetic utility of this method.

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Publication Details

Journal
Organic Letters
Published
2025-01-16
DOI
https://doi.org/10.1021/acs.orglett.4c04625
Citations
1
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.94

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article

Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks

Cheng Peng, Yan‐Ling Ji, Gu Zhan, Bo Han et al.
1 citations
Organic Letters
Asymmetric Synthesis and Catalysis
0.94
article

Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks

Cheng Peng, Yan‐Ling Ji, Gu Zhan, Bo Han, Ke Xu, Heping Li, Qian‐Qian Yang
article en
1 citations

Abstract

Herein, we introduce a scandium-catalyzed synthetic strategy that provides access to a diverse and functionalized array of cyclobutene frameworks adorned with a quaternary carbon center. This approach broadens the synthetic repertoire of 2-alkynylnaphthols with alkenes, offering a versatile platform for the construction of complex molecular architectures. The asymmetric catalytic [2 + 2] cycloaddition reaction demonstrates a wide substrate scope and an impressive functional group tolerance, yielding products with high efficiency, up to 97% yield, and excellent enantiomeric excess of up to 97%. The simplicity of scaling up this process, coupled with the ease of converting these cyclobutene frameworks into a variety of substituted products, significantly enhances the synthetic utility of this method.

Organic LettersVol. 27(4)
Chengdu University of Traditional Chinese Medicine (CN)
National Natural Science Foundation of China, Department of Science and Technology of Sichuan Province, Chengdu University of Traditional Chinese Medicine
Openalex Percentile: Top 30%
Asymmetric Synthesis and Catalysis
0.94
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Sc-Catalyzed Asymmetric [2 + 2] Annulation of 2-Alkynylnaphthols with Dienes to Access Cyclobutene Frameworks — Cheng Peng, Yan‐Ling Ji, et al. · Organic Letters (2025) | TGRS Research Map | TGRS