143746-17-2

Upstream product

• 100-44-7 benzyl chloride 
• 101-06-4 N,N-dibenzyl-2-aminoethanol 
• 75-77-4 chloro-trimethyl-silane 
• 143746-13-8 2-(N,N-Dibenzylamino)ethyl 2,2,4,4-tetramethyl-1,3-oxazolidine-3-carboxylate 

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.

Preparation of sec. or tert. alcohols

A process for the preparation of a compound of the formula STR1 which comprises deprotonating a carbamate of the formula STR2 in an inert solvent with a selective base, in the presence of a chelate-forming diamine to give a compound of the formula STR3 and then reacting III in an inert solvent, either with an achiral electrophile of the formula (IV) or (V) or with an optionally prochiral electrophile of the formula (VI) STR4 and in the case in which R1 represents an electrofugic leaving group, optionally again electrophilically substituted with the formation of an acyl anion and renewed deprotonation, and in a last step, solvolytically removing the protecting group --CO--NR10 R11.