Phosphazene-Catalyzed Regioselective Condensation of Allyl Thioethers with Aldehydes: A Rapid Approach to 1,3-Dienyl Sulfides, -Sulfoxides and -Sulfones

Synthesis DOI: 10.1055/a-2259-5395 The phosphazene-catalyzed regioselective condensation of allyl thioethers with aldehydes is investigated. Upon treatment of allyl thioethers with P4-t-Bu, allyl thioether anions are generated and rapidly react with aromatic aldehydes, leading to 1,3-dienyl sulfides in good yields with high regioselectivity. This finding provides an alternative approach for the preparation of allyl thioether anions in a regioselective manner. In addition, chemoselective transformations of 1,3-dienyl sulfides to provide the corresponding 1,3-dienyl sulfoxides or 1,3-dienyl sulfones are also demonstrated. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - February 27, 2024 Category: Chemistry Authors: Phae-nok, Supasorn Kuhakarn, Chutima Leowanawat, Pawaret Reutrakul, Vichai Soorukram, Darunee Tags: paper Source Type: research