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Updated: Jun 20, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
11:09

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation

Published on: August 1, 2018

Solid-phase synthesis of peptidyl thioacids employing a 9-fluorenylmethyl thioester-based linker in conjunction with

David Crich1, Kasinath Sana

  • 1Centre de Recherche de Gif-sur-Yvette, Institut de Chimie des Substances Naturelles, Centre National de la Recherche Scientifique, avenue de la Terrasse, 91198 Gif-sur-Yvette, France. dcrich@icsn.cnrs-gif.fr

The Journal of Organic Chemistry
|September 4, 2009
PubMed

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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
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