A Practical Synthesis of Geometrically Pure N-Boc-Protected Primary  Allylic Amines

Rolf A. T. M. van Benthem; Jasper J. Michels; Henk Hiemstra; W. Nico Speckamp

doi:10.1055/s-1994-22857

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Synlett 1994; 1994(5): 368-370
DOI: 10.1055/s-1994-22857

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A Practical Synthesis of Geometrically Pure N-Boc-Protected Primary Allylic Amines

Rolf A. T. M. van Benthem^* , Jasper J. Michels, Henk Hiemstra, W. Nico Speckamp

^*Laboratory of Organic Chemistry, University of Amsterdam, Nieuwe Achtergracht 129, 1018 WS Amsterdam, The Netherlands

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Publikationsdatum:
22. März 2002 (online)

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N-Boc-Protected primary allylic amines are easily prepared from the corresponding mesylates or halides by using di-tert-butyl imidodicarbonate (Boc₂NH) and K₂CO₃ or Cs₂CO₃ in a Gabriel-type substitution, followed by selective removal of one Boc group with TFA.