1379586-33-0

Upstream product

• 62-53-3 aniline 
• 60656-87-3 benzyloxyacetoaldehyde 
• 622-08-2 2-Benzyloxyethanol 
• 1379586-20-5 (E)-benzyl 4-(benzyloxy)-but-2-enoylcarbamate 
• 1379586-32-9 (R)-(-)-2-(benzyloxymethyl)-1-methyl-2,3-dihydroquinolin-4(1H)-one 
• 1379586-31-8 2-(benzyloxymethyl)-1-methyl-1,2,3,4-tetrahydroquinolin-4-amine 
• 1379586-30-7 (2R,4R)-(+)-methyl 2-(benzyloxymethyl)-1-methyl-1,2,3,4-tetrahydroquinolin-4-ylcarbamate 
• 1379586-29-4 (2R,4R)-(-)-(2-benzyloxymethyl-1,2,3,4-tetrahydroquinolin-4-yl)-carbamic acid methyl ester 
• 1379586-24-9 (R)-(+)-benzyl 4-(benzyloxy)-3-(phenylamino)-butanoylcarbamate 

Relevant academic research and scientific papers

Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction

An optically active tetrahydroquinoline intermediate (5) was prepared in 8 steps from monoprotected ethylene glycol, using a Pd-catalysed aza-Michael reaction to induce chirality. This can be transformed into three Galipea alkaloids (angustureine, galipeine and cuspareine). The proximity of a benzyloxy group is found to exert profound effects in several steps of the synthesis.