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  • Title: Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters.
    Author: Benedetti F, Berti F, Fanfoni L, Garbo M, Regini G, Felluga F.
    Journal: Molecules; 2016 Jun 21; 21(6):. PubMed ID: 27338326.
    Abstract:
    The 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.
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