Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates

Allenoates are versatile reagents that can be used for numerous (formal) cycloaddition reactions under (chiral) Lewis base catalysis. Most commonly, the catalysts of choice are phosphines, amines, and <i>N</i>-heterocyclic carbenes. We have recently established the use of readily available chiral isochalcogenoureas as catalysts for asymmetric (4 + 2)-heterocycloadditions of allenoates with various vinylogous acceptors. This represents a complementary approach for allenoate activation and gives access to various highly functionalized chiral dihydropyrans with good to excellent enantioselectivities and diastereoselectivities.

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Publication Details

Journal
Chemistry Letters
Published
2024-08-23
DOI
https://doi.org/10.1093/chemle/upae168
Citations
7
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
1.75

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article

Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates

Mario Waser
7 citations
Chemistry Letters
Asymmetric Synthesis and Catalysis
1.75
article

Isochalcogenourea-catalyzed asymmetric (4 + 2)-heterocycloadditions of allenoates

Mario Waser
article en
7 citations

Abstract

Allenoates are versatile reagents that can be used for numerous (formal) cycloaddition reactions under (chiral) Lewis base catalysis. Most commonly, the catalysts of choice are phosphines, amines, and <i>N</i>-heterocyclic carbenes. We have recently established the use of readily available chiral isochalcogenoureas as catalysts for asymmetric (4 + 2)-heterocycloadditions of allenoates with various vinylogous acceptors. This represents a complementary approach for allenoate activation and gives access to various highly functionalized chiral dihydropyrans with good to excellent enantioselectivities and diastereoselectivities.

Chemistry LettersVol. 53(9)
Johannes Kepler University of Linz (AT)
Österreichische Nationalstiftung für Forschung, Technologie und Entwicklung, Austrian Science Fund
Clean water and sanitation
Openalex Percentile: Top 16%
Asymmetric Synthesis and Catalysis
1.75
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