Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates

Piringer, Magdalena; Stockhammer, Lotte; Vogl, Lukas; Weinzierl, David; Zebrowski, Paul; Waser, Mario

doi:10.1016/j.tchem.2024.100063

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2024

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Cited by 2 publications

References 93 publications

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

Waser

2024

Chemistry Letters

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

Waser

2024

Chemistry Letters

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Chiral Lewis Bases for Asymmetric Organocatalysis

Waser

2024

Preprint

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Chiral Lewis bases (LBs) are versatile nucleophilic organocatalysts that allow for numerous highly enantioselective transformations. Over the last years our group had a strong interest in the utilization of chiral LBs (i.e. isothioureas, phosphines, amines) for the activation and control of simple carboxylic acid derivatives (via in situ C1 ammonium enolate formation) and allenoates (via in situ betaine formation) for numerous applications. In this presentation I will give an overview of our most recent results, presenting past and ongoing investigations focusing on the development and mechanistic understanding of new cyclization reactions as well as new a-functionalization chemistry.

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Enantioselective α-heterofunctionalization reactions of catalytically generated C1-Lewis base enolates

Cited by 2 publications

References 93 publications

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

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

Chiral Lewis Bases for Asymmetric Organocatalysis

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