249923-10-2

Upstream product

• 249922-96-1 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (1S,2S)-1-benzoyl-2-dibenzylamino-3-phenyl-propyl ester 
• 100-52-7 benzaldehyde 
• 247575-73-1 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-3-phenyl-propyl ester 
• 146176-60-5 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carbonyl chloride 
• 111060-52-7 (S)-2-(dibenzylamino)-3-phenylpropan-1-ol 
• 63-91-2 L-phenylalanine 
• 111138-83-1 N,N-dibenzyl-L-phenylalanine benzyl ester 

Downstream Products

• 249923-25-9 (1R,2S,3S)-3-Dibenzylamino-1,4-diphenyl-butane-1,2-diol 

Relevant academic research and scientific papers

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.