Download PDF
Synthesis 1988; 1988(8): 587-592
DOI: 10.1055/s-1988-27645
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Secondary Allylic Amines

Norbert De Kimpe* , Elena Stanoeva, Roland Verhé, Niceas Schamp
  • *Laboratory of Organic Chemistry, Faculty of Agricultural Sciences, State University of Gent, Coupure Links 653, B-9000 Gent, Belgium
Further Information

Publication History

Publication Date:
20 August 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Secondary allylic amines were synthesized from aldehydes and primary amines via successive conversion into aldimines, α-haloaldimines and α,β-unsaturated aldimines, the latter being selectively reduced by sodium borohydride at the imino function. This method allowed the synthesis of secondary allylic amines with high preponderance of the E-stereochemistry. A comparison was made with an alternative method involving the generation of α,β-unsaturated aldimines from α,β-unsaturated aldehydes and primary amines, and subsequent borohydride reduction.