2.4 1,3-Dipolar Cycloadditions Involving Carbonyl or Azomethine Ylides

X. Xu; W. Hu

Abstract

Carbonyl ylides, which behave as active 1,3-dipole species, have found numerous applications in organic synthesis, especially in the formation of five-membered heterocycles. Among the versatile transformations of carbonyl ylides, 1,3-dipolar cycloadditions with π-bonds, including (3 + 2)-cycloaddition reactions with carbon–carbon π-bonds, aldehydes, and imines, are ubiquitous and important reactions. This chapter focuses on recent advances in these catalytic (3 + 2)-cycloaddition reactions and the examples presented emphasize the chemo-, diastereo-, and enantiocontrol that can be achieved. Also described are selected examples of cycloaddition reactions with azomethine ylides, which behave with similar reactivity to carbonyl ylides, to give the corresponding N-heterocycles. In addition, some selected applications of these (3 + 2)-cycloaddition reactions in natural product synthesis are highlighted.

Key words

(3 + 2) cycloaddition - carbonyl ylides - azomethine ylides - 1,3-dipoles - diazo compounds - chiral dirhodium carboxylates - heterocycles - five-membered rings - natural product synthesis - asymmetric catalysis

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