Convergent synthesis of pyrrolidines, piperidines, perhydroazepines and tetrahydroisoquinolines via zirconocene η 2-imine complexes

MCJ Harris, RJ Whitby, J Blagg

Index: Harris, Michael C. J.; Whitby, Richard J.; Blagg, Julian Tetrahedron Letters, 1995 , vol. 36, # 24 p. 4287 - 4290

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Citation Number: 15

Abstract

Zirconocene η2-imine complexes formed by a C H activation route from a variety of amines are trapped by ω-halo-alkenes or-alkynes to afford 2, 3-disubstituited pyrrolidines, piperidines and perhydroazepines on work up and cyclisation. In some cases it was necessary to use a protected hydroxyl group rather than the halide and cyclise in a separate step through selective formation of the O-mesylate.