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Synlett 2000; 2000(1): 77-79
DOI: 10.1055/s-2000-6437
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Chemoselective Oxidative Debenzylation of N,N-Dibenzylamines

Benno Hungerhoff* , Subhendu S. Samanta, Jochen Roels, Peter Metz
  • *Institut für Organische Chemie, Technische Universität Dresden, Mommsenstraße 13, D-01062 Dresden, Germany; Fax +49 3 51 4 63 31 62; E-mail: metz@coch01.chm.tu-dresden.de
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Publication Date:
31 December 2000 (online)

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Tertiary amines incorporating two N-benzyl substituents are readily mono-debenzylated with CAN or DDQ. An N,N-dibenzyl derivative of a dienylamine with a homoallylic C-N bond is smoothly deblocked by DDQ as well, whereas CAN leads to fragmentation in this case.

amines - oxidations - protecting groups - conjugate additions - copper

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