Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
AbstractThe four-step conversion of a series of N-Boc-protected l-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes. View Full-Text
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Benedetti, F.; Berti, F.; Fanfoni, L.; Garbo, M.; Regini, G.; Felluga, F. Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters. Molecules 2016, 21, 805.
Benedetti F, Berti F, Fanfoni L, Garbo M, Regini G, Felluga F. Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters. Molecules. 2016; 21(6):805.Chicago/Turabian Style
Benedetti, Fabio; Berti, Federico; Fanfoni, Lidia; Garbo, Michele; Regini, Giorgia; Felluga, Fulvia. 2016. "Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters." Molecules 21, no. 6: 805.
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