TY - JOUR T1 - Enantioselective organocatalytic reduction of β-trifluoromethyl nitroalkenes: an efficient strategy for the synthesis of chiral β-trifluoromethyl amines. AU - Massolo,Elisabetta, AU - Benaglia,Maurizio, AU - Orlandi,Manuel, AU - Rossi,Sergio, AU - Celentano,Giuseppe, Y1 - 2015/01/08/ PY - 2014/10/20/received PY - 2015/1/10/entrez PY - 2015/1/13/pubmed PY - 2015/12/15/medline KW - bifunctional catalyst KW - chiral fluorinated amines KW - nitroalkenes KW - reduction KW - trifluoromethyl derivatives SP - 3589 EP - 95 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 21 IS - 9 N2 - An efficient organocatalytic stereoselective reduction of β-trifluoromethyl-substituted nitroalkenes, mediated by 3,5-dicarboxylic ester-dihydropyridines (Hantzsch ester type), has been successfully developed. A multifunctional thiourea-based (S)-valine derivative was found to be the catalyst of choice, promoting the reaction in up to 97% ee. The methodology has been applied to a wide variety of substrates, leading to the formation of differently substituted precursors of enantiomerically enriched β-trifluoromethyl amines. The mechanism of the reaction and the mode of action of the metal-free catalytic species were computationally investigated; on the basis of DFT transition-state (TS) analysis, a model of stereoselection was also proposed. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/25573847/Enantioselective_organocatalytic_reduction_of_β_trifluoromethyl_nitroalkenes:_an_efficient_strategy_for_the_synthesis_of_chiral_β_trifluoromethyl_amines_ DB - PRIME DP - Unbound Medicine ER -