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Synlett 1995; 1995(9): 949-951
DOI: 10.1055/s-1995-5128
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Synthesis of N-p-Toluenesulphonyl-2-alkenyl Aziridines by Regioselective Aziridination of 1,3-Dienes

J. G. Knight* , M. P. Muldowney
  • *Department of Chemistry, Bedson Building, The University of Newcastle upon Tyne, NE1 7RU, U.K.
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Publication Date:
31 December 2000 (online)

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The regioselective copper catalysed aziridination of 1,3-dienes using PhI=NTs is reported. For unsymmetrical dienes, the major product is that resulting from reaction of the more electron rich double bond. When the two double bonds are electronically similar, steric hindrance governs the selectivity. In some cases rearrangement of the vinyl aziridine to the corresponding 3-pyrroline was observed. The reaction of 1,3-cyclooctadiene gave the 3-pyrroline (5) exclusively.

Vinylaziridine - 3-pyrroline - nitrene - 1,3-diene - regioselective - copper catalysed

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