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Keywords:

  • asymmetric synthesis;
  • homogeneous catalysis;
  • isocyanides;
  • multicomponent reactions;
  • nitrogen heterocycles
Thumbnail image of graphical abstract

Three-part harmony: Three-component Passerini reactions (P-3CR, see Scheme) of a wide range of aldehydes 2 and isocyanides 3, with hydrazoic acid 4 in toluene, in the presence of a [(salen)AlMe]-complex catalyst afford 5-(1-hydroxyalkyl)tetrazoles 1 in good-to-excellent yields and enantiomeric excess. A tandem Michael addition/enantioselective P-3CR, using an acrolein substrate, affords highly functionalized tetrazoles.