title: Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters.
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.
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy. benedett@units.it.
authors.forename: Fabio
authors.initials: F
authors.lastname: Benedetti
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy. fberti@units.it.
authors.forename: Federico
authors.initials: F
authors.lastname: Berti
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy. lidia.fanfoni@gmail.com.
authors.forename: Lidia
authors.initials: L
authors.lastname: Fanfoni
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy. garb.michele@gmail.com.
authors.forename: Michele
authors.initials: M
authors.lastname: Garbo
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy. giorgia.regini@phd.units.it.
authors.forename: Giorgia
authors.initials: G
authors.lastname: Regini
authors.affiliation: Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy. ffelluga@units.it.
authors.forename: Fulvia
authors.initials: F
authors.lastname: Felluga
mesh_terms: D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000499:Allylamine / Q000138:chemical synthesis* / Q000737:chemistry; D000596:Amino Acids / Q000737:chemistry; D003516:Cycloparaffins / Q000737:chemistry; D008738:Methyl Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry
chemical_list: D000447:Aldehydes; D000596:Amino Acids; D003516:Cycloparaffins; D008738:Methyl Ethers; D013450:Sulfones; D000499:Allylamine
keywords: acylation; allylamines; amino acids; chiral pool; sulfones