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

作者：De Risi Carmela^*; Benetti Simonetta; Fogagnolo Marco; Bertolasi Valerio

来源：Tetrahedron Letters, 2013, 54(4): 283-286.

DOI：10.1016/j.tetlet.2012.10.134

• Domino reactions
• Diastereoselectivity
• Cyclopropanes
• S-Heterocycles

An unprecedented domino Michael/alpha-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.

• 出版日期2013-1-23