Thioureas bearing electron-deficient aryl groups show high catalytic activity in the biomimetic bromocyclization of geranyl derivatives. The reaction of geranyl derivatives with N-bromosuccinimide (NBS) proceeds rapidly in CH 2 Cl 2 to give the corresponding bromocyclization products in high yields as a ca. 1:1 mixture of endo- A nd exo-isomers. The reactivity of geranyl derivatives highly depends on the terminal substituent: Electron-donating substituents increase the reactivity, while electron-withdrawing substituents decrease the reactivity.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry