New insights into NIS-promoted aminocyclization. Synthesis of decahydroquinolines from 2-allylcyclohexylamines.
Bishomoallylic secondary amines embodying the 2-allyl-N-benzylcyclohexylamine unit react with NIS to undergo cyclization through 6-endo processes in either the cis or trans series. Nevertheless, when the resulting cis-3-iododecahydroquinolines are treated with Al2O3, the exo derivatives evolve into octahydroindoles and the endo derivatives keep the same backbone, the configuration being retained in the generated alcohols.
Diaba
Faïza
F
Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain.
Ricou
Eva
E
Bonjoch
Josep
J
D000588:Amines / Q000138:chemical synthesis*; D003500:Cyclization; D003514:Cyclohexylamines / Q000737:chemistry*; D007202:Indicators and Reagents; D009532:Nickel / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*
D000588:Amines; D003514:Cyclohexylamines; D007202:Indicators and Reagents; D011804:Quinolines; D009532:Nickel; C017558:nickel sulfide