Tetrahedron

4, 4′-Di-tert-butylbiphenyl-catalysed reductive opening of azetidines with lithium: A direct preparation of 3, N-dilithioalkylamines

J Almena, F Foubelo, M Yus

文献索引：Almena, Juan; Foubelo, Francisco; Yus, Miguel Tetrahedron, 1994 , vol. 50, # 19 p. 5775 - 5782

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被引用次数: 50

摘要

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) 5C O, PhCH NPh, CO2) yields, after hydrolysis with water, the expected functionalysed amines 3aa-ah. The same method applied to N-isopropyl-2-phenylazetidine 1 c affords ...