Article ID Journal Published Year Pages File Type
5214820 Tetrahedron 2015 7 Pages PDF
Abstract

A sulfonyl-stabilized diazoketone underwent an efficient rhodium-catalyzed cascade reaction with an internal vinylsulfonate unit to give a tricyclic sultone as a single diastereomer. Nucleophilic addition of a vinyl Grignard reagent to the ketone of the resultant arylsulfonyl-substituted cycloadduct was stereocomplementary with respect to vinyl Grignard addition to corresponding ester-substituted substrates. The latter tricyclic compounds were chemoselectively transformed into vinylsultones via β-elimination in good yield.

Graphical abstractFigure optionsDownload full-size imageDownload high-quality image (65 K)Download as PowerPoint slide

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry