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
Molecules 2016, 21(6), 805; https://doi.org/10.3390/molecules21060805
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)
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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Keywords:
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
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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.
AMA 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(6):805.
Chicago/Turabian StyleBenedetti, 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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