The synthesis of (±)-heliotridane and (6S,7S)-dihydroxyheliotridane via sequential hydrogen atom abstraction and cyclisation

Article abstract of DOI:10.1016/0040-4039(96)01237-3

Treatment of N-(3-bromo-3-butenyl)pyrrolidine derivatives with tributyltin hydride and AIBN leads to hydrogen atom transfer of the intermediate vinyl radicals to give α-amino radicals which then cyclise stereoselectively yielding pyrrolizidines 1 and 13.