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

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 elim...

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Autores principales: Benedetti, Fabio, Berti, Federico, Fanfoni, Lidia, Garbo, Michele, Regini, Giorgia, Felluga, Fulvia
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273449/
https://www.ncbi.nlm.nih.gov/pubmed/27338326
http://dx.doi.org/10.3390/molecules21060805
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author Benedetti, Fabio
Berti, Federico
Fanfoni, Lidia
Garbo, Michele
Regini, Giorgia
Felluga, Fulvia
author_facet Benedetti, Fabio
Berti, Federico
Fanfoni, Lidia
Garbo, Michele
Regini, Giorgia
Felluga, Fulvia
author_sort Benedetti, Fabio
collection PubMed
description 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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spelling pubmed-62734492018-12-28 Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters Benedetti, Fabio Berti, Federico Fanfoni, Lidia Garbo, Michele Regini, Giorgia Felluga, Fulvia Molecules Article 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. MDPI 2016-06-21 /pmc/articles/PMC6273449/ /pubmed/27338326 http://dx.doi.org/10.3390/molecules21060805 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Benedetti, Fabio
Berti, Federico
Fanfoni, Lidia
Garbo, Michele
Regini, Giorgia
Felluga, Fulvia
Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
title Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
title_full Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
title_fullStr Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
title_full_unstemmed Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
title_short Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters
title_sort synthesis of chiral, enantiopure allylic amines by the julia olefination of α-amino esters
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273449/
https://www.ncbi.nlm.nih.gov/pubmed/27338326
http://dx.doi.org/10.3390/molecules21060805
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