Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.

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Publication Details

Journal
Synlett
Published
2025-07-18
DOI
https://doi.org/10.1055/a-2659-8340
Citations
2
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
1.87
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article

Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

Magdalena Piringer, Anna Scheucher, Mario Hofer, Mario Waser et al.
2 citations
Synlett
Asymmetric Synthesis and Catalysis
1.87
article

Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

Magdalena Piringer, Anna Scheucher, Mario Hofer, Mario Waser, Lukas S. Vogl
article en
2 citations

Abstract

We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.

SynlettVol. 36(19)
Johannes Kepler University of Linz (AT), Kepler Universitätsklinikum (AT)
Clean water and sanitation
Openalex Percentile: Top 14%
Asymmetric Synthesis and Catalysis
1.87
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