Tetrahedron Letters

[3+ 2] Dipolar cycloadditions of an unstabilised azomethine ylide under continuous flow conditions

M Grafton, AC Mansfield, MJ Fray

Index: Grafton, Mark; Mansfield, Andrew C.; Fray, M. Jonathan Tetrahedron Letters, 2010 , vol. 51, # 7 p. 1026 - 1029

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Citation Number: 26

Abstract

The [3+ 2] dipolar cycloaddition reactions of the unstabilised azomethine ylide precursor benzyl (methoxymethyl)(trimethylsilylmethyl) amine with 12 electron-deficient alkenes in the presence of catalytic trifluoroacetic acid are examined under continuous flow conditions (20– 100° C, 10–60min residence time). The more reactive and hazardous alkenes such as ethyl acrylate, N-methylmaleimide and (E)-2-nitrostyrene afford substituted N-benzylpyrrolidine ...