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

作者：Peter R. Schreiner, Friedemann Dressler, Victoria Öhler, Christopher Topp · 发表于：Synlett · 年份：2023 · DOI：10.1055/a-2216-4710 · 被引用次数：8 · 研究领域：Chemical Synthesis and Reactions、Synthesis and Catalytic Reactions、Asymmetric Synthesis and Catalysis

Abstract 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.