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 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.



Titolo: Synthesis of chiral, enantiopure allylic amines by the Julia olefination of α-amino esters
Autori: 
BENEDETTI, FABIO
BERTI, FEDERICO
FANFONI, LIDIA
GARBO, MICHELE
REGINI, GIORGIA
FELLUGA, FULVIA
Data di pubblicazione: 2016
Rivista: 
MOLECULES  
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.
Handle: http://hdl.handle.net/11368/2877016
Digital Object Identifier (DOI): http://dx.doi.org/10.3390/molecules21060805
URL: http://www.mdpi.com/1420-3049/21/6/805
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