ArticleJournal of the American Chemical Society2022
Deployment of Sulfinimines in Charge-Accelerated Sulfonium Rearrangement Enables a Surrogate Asymmetric Mannich Reaction.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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11 citing papers in PubMed.
- Light-Driven Epimerization: Diastereoconvergent Synthesis of [Angewandte Chemie (International ed. in English) · 2026Article
- Synthesis of Sterically Congested Carbonyl Compounds via anJournal of the American Chemical Society · 2025Article
- PotassiumChemical science · 2025Article
- Asymmetric Synthesis of β-Ketoamides by Sulfonium Rearrangement.Angewandte Chemie (International ed. in English) · 2024Article
- Review
- Domino Conjugate Addition-1,4-Aryl Migration for the Synthesis of α,β-Difunctionalized Amides.JACS Au · 2024Article
- Free Amino Group Transfer via α-Amination of Native Carbonyls.Angewandte Chemie (International ed. in English) · 2023Article
- Transfer freier Aminogruppen via α-Aminierung von Carbonylen.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2023Article
- Article
- Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes.Organic letters · 2022Article
- Multicatalysis protocol enables direct and versatile enantioselective reductive transformations of secondary amides.Science advances · 2022Article
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5 authors.
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Abstract
β-Amino acid derivatives are key structural elements in synthetic and biological chemistry. Despite being a hallmark method for their preparation, the direct Mannich reaction encounters significant challenges when carboxylic acid derivatives are employed. Indeed, not only is chemoselective enolate formation a pitfall (particularly with carboxamides), but most importantly the inability to reliably access α-tertiary amines through an enolate/ketimine coupling is an unsolved problem of this century-old reaction. Herein, we report a strategy enabling the first direct coupling of carboxamides with ketimines for the diastereo- and enantioselective synthesis of β-amino amides. This conceptually novel approach hinges on the innovative deployment of enantiopure sulfinimines in sulfonium rearrangements, and at once solves the problems of chemoselectivity, reactivity, and (relative and absolute) stereoselectivity of the Mannich process. In-depth computational studies explain the observed, unexpected (dia)stereoselectivity and showcase the key role of intramolecular interactions, including London dispersion, for the accurate description of the reaction mechanism.
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