181946-22-5Relevant academic research and scientific papers
Intramolecular nucleophilic deselenenylation reactions promoted by benzeneselenenyl triflate. Stereospecific synthesis of vicinal amino alcohol precursors
Tingoli, Marco,Testaferri, Lorenzo,Temperini, Andrea,Tiecco, Marcello
, p. 7085 - 7091 (2007/10/03)
After activation with electrophilic selenenylating agents, the phenylseleno group of vicinal azido selenides, containing internal oxygen or nitrogen nucleophilic substituents, readily undergoes intramolecular nucleophilic displacement to afford azido-substituted heterocyclic compounds. This intramolecular substitution occurs with inversion of configuration at the carbon atom bearing the selenium atom. Starting from acetamido selenides and carbamato selenides, a stereocontrolled synthesis of the vicinal amino alcohol precursor oxazolines and oxazolidin-2-ones has been developed.
