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Synthesis 1988; 1988(8): 587-592
DOI: 10.1055/s-1988-27645
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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
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Publikationsdatum:
20. August 2002 (online)

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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.