799560-21-7Relevant 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.
Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones
Pico, Anna,Moyano, Albert,Pericas, Miquel A.
, p. 5075 - 5083 (2007/10/03)
A set of diversely substituted N-Boc-γ-amino vinyl sulfones has been prepared by a four-step procedure from readily available, highly enantiopure anti-N-Boc-3-amino-1,2-alkanediols. This new route, which does not depend on the accessibility of α-amino acids as starting materials, is noteworthy for its efficiency, for its generality, and for the fact that both enantiomers of a given γ-amino vinyl sulfone can be obtained with equal ease.