L–Cysteine‐Catalysed Hydration of Activated Alkynes

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Abstract: Hydration reactions consist of the introduction of a molecule of water into a chemical compound and are particularly useful to transform alkynes into carbonyls, which are strategic intermediates in the synthesis of a plethora of compounds. Herein we demonstrate that L–cysteine can catalyse the hydration of activated alkynes in a very effective and fully regioselective manner to access important building blocks in synthetic chemistry such as β‐ketosulfones, amides and esters, in aqueous media. The mild reaction conditions facilitated the integration with enzyme catalysis to access chiral β‐hydroxy sulfones from the corresponding alkynes in a one‐pot cascade process in good yields and excellent enantiomeric ratios. These findings pave the way towards establishing a general method for metal‐free, cost‐effective, and more sustainable alkyne hydration processes.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: L–Cysteine‐Catalysed Hydration of Activated Alkynes ; day:06 ; month:11 ; year:2024 ; extent:9
Angewandte Chemie ; (06.11.2024) (gesamt 9)

Creator: González‐Rodríguez, Jorge
González‐Granda, Sergio
Lavandera, Iván
Gotor‐Fernández, Vicente
Mangas‐Sánchez, Juan

DOI: 10.1002/ange.202414046

URN: urn:nbn:de:101:1-2411081318537.064867108034

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:27 AM CEST

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Associated

González‐Rodríguez, Jorge
González‐Granda, Sergio
Lavandera, Iván
Gotor‐Fernández, Vicente
Mangas‐Sánchez, Juan

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Platinum Catalysed Hydrostannylation of Terminal Alkynes; Highly Selective Synthesis of Vinyl Stannanes

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Using alcohols as simple H2-equivalents for copper-catalysed transfer semihydrogenations of alkynes

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Cobalt-Catalyzed Reductive Coupling of Activated Alkenes with Alkynes

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Novel aza-arylphosphane ligands for ruthenium catalyzed anti Markovnikov hydration of terminal alkynes

Hochschulschrift

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Shape Selectivity in the Gold‐Catalyzed Hydration of Alkynes Using a Cavity‐Shaped Phosphine

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Gold‐Catalysed Intramolecular Reaction of Alkynes with Sulfoximines Acting as N‐ and O‐Transfer Reagents

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