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Molecules 2016, 21(6), 805; doi:10.3390/molecules21060805

Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters

Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy
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Academic Editors: Carlo Siciliano and Constantinos M. Athanassopoulos
Received: 24 May 2016 / Revised: 14 June 2016 / Accepted: 14 June 2016 / Published: 21 June 2016
(This article belongs to the Special Issue Synthesis of Bioactive Compounds from the Chiral Pool)
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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. View Full-Text
Keywords: chiral pool; allylamines; amino acids; sulfones; acylation chiral pool; allylamines; amino acids; sulfones; acylation
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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