Asymmetric Synthesis of 5-(1-Hydroxyalkyl)tetrazoles by Catalytic Enantioselective Passerini-Type Reactions


  • We gratefully acknowledge the National Science Foundation of China (NSFC), the Chinese Academy of Science, and CNRS for financial support.


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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.