799560-34-2

Upstream product

• 799559-94-7 (2S,3S)-3-(tert-butoxycarbonylamino)-5-methyl-1-phenylthio-2-hexanol 
• 107202-52-8 (2S)-2-[(1S)-1-[N-(tert-butyloxycarbonyl)amino]-3-methylbutyl]oxirane 
• 154913-79-8 (2S,3S)-3-azido-5-methylhexane-1,2-diol 
• 112319-34-3 (2R,3R)-2,3-epoxy-5-methyl-1-hexanol 
• 96387-10-9 (2S,3S)-3-t-butoxycarbonylamino-2-hydroxy-5-methylhexanol 
• 3112-85-4 methylphenylsulfonate 
• 63096-02-6 N-tert-butoxycarbonyl-L-leucine methyl ester 

Relevant academic research and scientific papers

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.

Enantiodivergent, catalytic asymmetric synthesis of γ-amino vinyl sulfones

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.