NHC‐Catalyzed [3+3] Cycloaddition of 2‐(acetoxymethyl)buta‐2,3‐dienoates with 1 C,3O‐bisnucleophiles

Abstract Diverse transformations of allenoates catalyzed by Lewis bases have emerged as a powerful platform for generating new chemical entities in organic synthesis. Herein, an N ‐heterocyclic carbene (NHC) catalyzed [3+3] cyclization of 2‐(acetoxymethyl)buta‐2,3‐dienoates with 1 C,3O‐bisnucleophiles has been developed. This approach provides a facile method to synthesize highly functionalized 4 H ‐pyran derivatives with a broad substrate scope (31 examples, up to 83 % yield).

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Publication Details

Journal
Asian Journal of Organic Chemistry
Published
2024-10-09
DOI
https://doi.org/10.1002/ajoc.202400439
Citations
5
Primary Topic
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
Type
article
Field-Weighted Citation Impact
1.25

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article

NHC‐Catalyzed [3+3] Cycloaddition of 2‐(acetoxymethyl)buta‐2,3‐dienoates with 1 C,3O‐bisnucleophiles

Changsheng Yao, Wei Cao, Kai Zhang, Chenxia Yu
5 citations
Asian Journal of Organic Chemistry
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
1.25
article

NHC‐Catalyzed [3+3] Cycloaddition of 2‐(acetoxymethyl)buta‐2,3‐dienoates with 1 C,3O‐bisnucleophiles

Changsheng Yao, Wei Cao, Kai Zhang, Chenxia Yu
article en
5 citations

Abstract

Abstract Diverse transformations of allenoates catalyzed by Lewis bases have emerged as a powerful platform for generating new chemical entities in organic synthesis. Herein, an N ‐heterocyclic carbene (NHC) catalyzed [3+3] cyclization of 2‐(acetoxymethyl)buta‐2,3‐dienoates with 1 C,3O‐bisnucleophiles has been developed. This approach provides a facile method to synthesize highly functionalized 4 H ‐pyran derivatives with a broad substrate scope (31 examples, up to 83 % yield).

Asian Journal of Organic ChemistryVol. 13(12)
Jiangsu Normal University (CN)
National Natural Science Foundation of China, Natural Science Foundation of Jiangsu Province
Openalex Percentile: Top 22%
N-Heterocyclic Carbenes in Organic and Inorganic Chemistry
1.25
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