911061-52-4

Upstream product

• 911061-51-3 C₉H₁₁N₃O₂ 
• 133187-22-1 (2S)-2-(tert-butyldimethylsilyloxy)-2-phenylacetaldehyde 
• 133187-21-0 Methyl (S)-(+)-α-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-α-phenylacetate 
• 17199-29-0 (S)-Mandelic acid 
• 4392-24-9 Cinnamyl bromide 
• 911061-50-2 (2R,3S)-1-bromo-3-phenylpropane-2,3-diol 

Downstream Products

• 911061-53-5 2-chloro-N-((2S,3S)-2,3-dihydroxy-3-phenylpropyl)acetamide 
• 847805-32-7 (+)-(2S,3S)-2-[α-hydroxy(phenyl)methyl]morpholine-4-carboxylic acid tert-butyl ester 
• 847805-34-9 (+)-(2S,3S)-2-[α-(2-ethoxyphenoxy)phenylmethyl]morpholine-4-carboxylic acid tert-butyl ester 
• 911061-54-6 C₁₁H₁₃NO₃ 
• 911061-55-7 C₁₁H₁₅NO₂ 
• 71620-89-8 (S,S)-reboxetine 

Relevant academic research and scientific papers

Stereodivergent synthesis of all the four stereoisomers of antidepressant reboxetine

Chiral amino alcohol-copper(ii) catalysts Cu-L1c and Cu-ent-L1c were utilized to promote the diastereoselective nitroaldol reactions of chiral aldehydes (S)-3 or (R)-3 with nitromethane, which respectively led to the preferential formation of certain stereoisomer for nitro diol derivatives 4. Using this catalytic protocol, all the four stereoisomers of the antidepressant reboxetine were divergently prepared. The highest overall yield of this synthetic route reached up to 30.5% from aldehyde (S)-3.

Enantioselective synthesis of (+)-(S,S)-reboxetine

An efficient enantioselective synthesis leading directly to (+)-(S,S)-reboxetine has been described from commercially available trans-cinnammyl bromide using Sharpless asymmetric dihydroxylation as the key step. Georg Thieme Verlag Stuttgart.