Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
by
Fabio Benedetti *
, Federico Berti, Lidia Fanfoni, Michele Garbo, Giorgia Regini and Fulvia Felluga *
, Federico Berti, Lidia Fanfoni, Michele Garbo, Giorgia Regini and Fulvia Felluga *
Department of Chemical and Pharmaceutical Sciences, University of Trieste, via Giorgieri 1. 34127 Trieste, Italy
*
Authors to whom correspondence should be addressed.
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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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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