Organocatalytic, Chemoselective, and Stereospecific House –Meinwald Rearrangement of Trisubstituted Epoxides

We present a novel method for the chemoselective House–Meinwald rearrangement of trisubstituted epoxides under mild conditions with the use of simple perfluorinated disulfonimides as Brønsted acid catalysts. We isolated the α-quaternary aldehyde products in yields of 27–97% using catalyst loadings as low as 0.5 mol% on a scale of 1 mmol. In addition, we show the stereospecific rearrangement using an enantioenriched substrate, which makes this method suitable for applications in total synthesis of natural products. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - January 5, 2024 Category: Chemistry Authors: Dressler, Friedemann Öhler, Victoria Topp, Christopher Schreiner, Peter R. Tags: letter Source Type: research