192439-50-2

Upstream product

• 2935-35-5 (S)-2-phenylglycine 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 

Downstream Products

• 198635-23-3 ((S)-3-Dibenzylamino-2-oxo-3-phenyl-propyl)-phosphonic acid dimethyl ester 
• 198635-43-7 Benzyl-((1S,2S)-2-hydroxy-1,4-diphenyl-butyl)-carbamic acid benzyl ester 
• 198635-41-5 (E)-(1S,2S)-1-Dibenzylamino-1,4-diphenyl-but-3-en-2-ol 
• 198635-32-4 (E)-(S)-1-Dibenzylamino-1,4-diphenyl-but-3-en-2-one 
• 247575-74-2 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-2-phenyl-ethyl ester 
• 197142-90-8 (S)-2-(N,N-dibenzylamino)-2-phenyl-1-ethanol 

Relevant academic research and scientific papers

Diastereoselective reduction of β-ketophosphonates derived from amino acids. A new entry to enantiopure β-hydroxy-γ-aminophosphonate derivatives

The reduction of γ-N,N-dibenzylamino-β-ketophosphonates 4 derived from readily available (S)-tribenzylated amino acids was achieved with catecholborane at -20°C affording γ-amino-β-hydroxyphosphonates 5 in high diastereoselectivity and good chemical yield. These reactions provide a new entry to enantiomerically pure γ-amino-β-hydroxyphosphonates.

Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active β-amino alcohols via 1-oxy- substituted alkyllithium intermediates

A facile protocol for the electrophilic C-substitution (methylation, acylation, α-hydroxyalkylation, and carboxylation) of several 2-(N,N- dibenzylamino)alkan-1-ols via the carbamates 10 is reported. The stereochemistry of the lithiation is greatly influenced by the complexing diamine. The substrate-directed selection between the diastereotopic a-pro-R and pro-S protons in the TMEDA-assisted deprotonation is largely shifted towards pro-S-selectivity in the presence of (-)-sparteine (4). Each of both diastereomeric series is readily accessible in several cases.

Stereoselective synthesis of β-amino alcohols: Diastereoselective reduction of chiral α-amino enones derived from amino acids

α-Amino acids are doubly benzylated at nitrogen to give N,N-dibenzyl amino acids, which can readily be converted to α'-amino enones 3. The α'-amino enones are very resistant to racemization, and undergo highly diastereoselective reduction to afford chiral amino alcohols upon treatment with L-Selectride under non-chelation control.