169701-72-8Relevant articles and documents
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
, (2016/07/06)
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.