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Synlett 2000; 2000(7): 0967-0970
DOI: 10.1055/s-2000-6664
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A Chiral Imidazoline Nitrone; A Cycloaddition Route to Imidazoisoxazoles and Pyrroloimidazoles

Raymond C. F. Jones* , Jason N. Martin, Paul Smith
  • *Chemistry Department, Loughborough University, Loughborough, Leics, LE 11, 3TU, UK
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Publication Date:
31 December 2000 (online)

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A chiral imidazolinium 3-oxide has been prepared, that undergoes diastereoselective dipolar cycloaddition with alkenes to afford imidazo[1,2-b]isoxazoles; a suitable cycloadduct undergoes N-O cleavage and recyclisation leading to a pyrrolo[1,2-a]imidazole and thence potentially to pyrrolidines.

imidazoisoxazoles - nitrones - cycloadditions - heterocycles - bicyclic compounds