Diastereoselective nitrocyclopropanation of 2,5-dihydrothiophene-3-carbaldehydes

An unprecedented domino Michael/α-alkylation reaction between 2,5-dihydrothiophene-3-carbaldehydes and bromonitromethane is presented. This process, efficiently catalyzed by DL-proline in the presence of MeOH/NaOAc system, provides access to novel 6-nitro-3-thiabicyclo[3.1.0]hexane-1-carbaldehyde derivatives in good yields with good to excellent diastereoselectivities.

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