Juan Almena, F. Foubelo, M. Yus
1994
Citations
0
Influential Citations
36
Citations
Journal
Tetrahedron
Abstract
Abstract The reaction of N-phenylazetidine 1a with an excess of lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl (5 mol %) in THF at −15°C leads to the corresponding dianion 2a, which by treatment with different electrophiles (H2O, D2O, ButCHO, PhCHO, ( CH 2 ) 5 C O, PhCHNPh, CO2) yields, after hydrolysis with water, the expected functionalysed amines 3aa-ah. The same method applied to N-isopropyl-2-phenylazetidine 1 c affords compounds 3ca-ce (electrophiles: H2O, D2O, PhCHO, Me2CO, CH2CHCH2Br) resulting from the more stable benzylic intermediate 2c. Finally, the regiochemistry in the reductive opening of 2-methyl-N-phenylazetidine 1d followed by deuterolysis was studied: a mixture of both regioisomers 3da+3da′ was obtained, the ratio being the oposite as expected according to the stability of both intermediates 2d and 2d′.