1379586-19-2Relevant academic research and scientific papers
Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction
Taylor, Laura L.,Goldberg, Frederick W.,Hii, King Kuok Mimi
, p. 4424 - 4432 (2012)
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.
