Stereoselective synthesis of geminal bromofluoroalkenes by kinetically controlled selective conversion of oxaphosphetane intermediates.

ABSTRACT: Geminal bromofluoroalkenes are an important subclass of versatile organic interhalide, which can serve as useful synthetic precursors to monofluoroalkenes that are valuable amide group isosteres. Nonetheless, despite the vast advancement of olefination methodologies, the broadly applicable stereoselective synthesis remained elusive for geminal bromofluoroalkenes before our work. In particular, the seemingly straightforward Wittig-type approach with interhalogenated phosphorus ylide has been unsuccessful because of the difficulty in the diastereoselective oxaphosphetane formation. Here, we describe a conceptually distinctive strategy, by which the stereoselectivity is gained via the selective decomposition of the oxaphosphetane intermediates. The suitably identified phosphorus(III) reagent

SUBMITTER: Jin J 

PROVIDER: S-EPMC11804150 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature