Reactions of fluorinated silanes with 2-nitrocinnamates

The interaction of 2-nitrocinnamates with silicon reagents Me3SiRf (R-f = CF3, C2F5, and C6F5) promoted either by sodium acetate in DMF or by tetrabutylammonium acetate in dichloromethane has been described. The reactions proceed as conjugate addition of fluorinated carbanion at the C = C bond and afford 3-aryl-2-nitrobutanoates bearing a fluorinated substituent in good yields as diastereomeric mixtures in ratio from 1:1 to 1.6:1. (C) 2011 Elsevier B.V. All rights reserved.