Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 21, Issue 9, Pages 3589-3595Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405730
Keywords
bifunctional catalyst; chiral fluorinated amines; nitroalkenes; reduction; trifluoromethyl derivatives
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Funding
- COST action [CM9505]
- ZaCh Systems (Zambon Group)
- Universita' degli Studi di Milano
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An efficient organocatalytic stereoselective reduction of -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 -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.
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