ArticleAngewandte Chemie (International ed. in English)2026
Sulfur-Directed Construction of Vinyl Cyclopropanes from 1,3-Dienes.
Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The stereoselective cyclopropanation of 1,3-dienes remains a long-standing challenge in the preparation of vinyl cyclopropanes (VCPs) due to the intrinsic electronic and steric bias of the diene scaffold. We report a sulfur-directed strategy that enables highly site- and diastereoselective cyclopropanation of S-substituted 1,3-dienes with diazo reagents under Cu-catalyzed reaction conditions. This unprecedented approach overrides the innate reactivity of the 1,3-diene through a thioether-directed reaction mode, providing rapid access to a broad library of highly functionalized S-VCPs obtained as single regio- and diastereomers. Preliminary mechanistic studies indicate a pericyclic cascade involving a 6π-electrocyclization and a [2,3]-sigmatropic rearrangement and postmodifications permit streamlined access to complex VCPs that remain inaccessible through conventional cyclopropanation techniques.
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