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

Organic & Biomolecular Chemistry
Laura L TaylorKing Kuok Mimi Hii

Abstract

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.

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Citations

Jan 16, 2016·Chemistry : a European Journal·Sonja KohrtJán Cvengroš
Jul 31, 2013·Natural Product Reports·Zacharias AmaraDelphine Joseph
Mar 29, 2013·Chemical Communications : Chem Comm·Andrey E SheshenevKing Kuok Mimi Hii
Apr 10, 2019·Chemical Reviews·Isravel MuthukrishnanJ Carlos Menéndez
Aug 16, 2017·The Journal of Organic Chemistry·Stephen G DaviesJames E Thomson

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