N-Cyanomethyl-β-chloroamines: a convenient source of aziridinium ions

[Display omitted] N-Cyanomethyl-β-chloroamines smoothly react with a range of alcohols or amines to give regio- and stereoselectively 1,2-aminoethers or 1,2-diamines. The reaction proceeds through the formation of an intermediate aziridinium ion. The N-cyanomethyl group can then be cleaved easily.

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 13; pp. 2253 - 2257
Main Authors Couty, François, Evano, Gwilherm, Prim, Damien
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 28.03.2005
Elsevier
Subjects
1,2-Aminoethers
1,2-Diamines
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
1,2-Aminoethers
1,2-Diamines
1,2-diamines
REARRANGEMENT
DEPROTONATION
OXIDE
1,2-aminoethers
SELECTIVE SYNTHESES
PSEUDOEPHEDRINE
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Summary:[Display omitted] N-Cyanomethyl-β-chloroamines smoothly react with a range of alcohols or amines to give regio- and stereoselectively 1,2-aminoethers or 1,2-diamines. The reaction proceeds through the formation of an intermediate aziridinium ion. The N-cyanomethyl group can then be cleaved easily.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.02.016