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.
Diastereoselective nitrocyclopropanation of 2,5-dihydrothiophene-3-carbaldehydes
DE RISI, Carmela
Primo
;BENETTI, SimonettaSecondo
;FOGAGNOLO, MarcoPenultimo
;BERTOLASI, ValerioUltimo
2013
Abstract
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.File in questo prodotto:
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