Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France.
Org Lett. 2021 Jan 1;23(1):247-252. doi: 10.1021/acs.orglett.0c04023. Epub 2020 Dec 18.
An efficient and straightforward gold-catalyzed protocol for the synthesis of 2-substituted 4-oxo-4-arylbutanal derivatives from commercially available or easily accessible alkynes and vinylsulfoxide substrates has been developed. Extension of the methodology to the use of 1-cycloalkenyl sulfoxides allowed the facile synthesis of five-, six-, and seven-membered-ring cycloalkyl-1-one backbone. Subsequently, the tetrahydrocycloalkyl[]pyrrole derivatives, which are found in many active pharmaceutical ingredients, were isolated in good yields. Mechanistic investigation highlighted a [3,3]-sigmatropic rearrangement of a sulfonium intermediate in this process.
已开发出一种从商业可得或易于获得的炔烃和乙烯砜底物合成 2-取代的 4-氧代-4-芳基丁醛衍生物的高效且直接的金催化方法。该方法的扩展可用于使用 1-环烯基砜，从而可轻松合成五元、六元和七元环环烷基-1-酮骨架。随后，在该过程中分离出了许多活性药物成分中存在的四氢环烷基[]吡咯衍生物，产率良好。机理研究强调了该过程中硫翁中间体的[3,3]-σ重排。
