Nitrogen-containing remote functionalised organolithium compounds by reductive opening of five- and six-membered heterocycles
1996; Elsevier BV; Volume: 52; Issue: 25 Linguagem: Inglês
10.1016/0040-4020(96)00397-3
ISSN1464-5416
AutoresJuan Almena, Francisco Foubelo, Miguel Yus,
Tópico(s)Asymmetric Hydrogenation and Catalysis
ResumoThe reaction of different five- or six-membered nitrogen-containing heterocycles such as N-isopropyl-2-phenylpyrrolidine (1), N-phenyl-3-pyrroline (6), N-phenylisoindoline (10), N-phenyltetrahydroisoquinoline (13) and N-methyltetrahydroisoquinoline (19) with an excess of lithium powder and a catalytic amount of DTBB (4.5 mol %), followed by treatment with electrophiles [H2O, D2O, MeI, CH2CHCH2Br, PriCHO, ButCHO, PhCHO, Me2CO, PrnCOMe, PhCOMe, (CH2)4CO, (CH2)5CO, CO2] and final hydrolysis gives a wide series of functionalised amines 3, 8, 9, 12 and 19, the key step in the process, being the reductive opening of the starting material giving a dianionic remote functionalised organolithium compound.
Referência(s)