通过对映选择性氮杂迈克尔加成反应不对称合成 2-烷基取代的四氢喹啉。
Asymmetric synthesis of 2-alkyl-substituted tetrahydroquinolines by an enantioselective aza-Michael reaction.
机构信息
Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, UK.
出版信息
Org Biomol Chem. 2012 Jun 14;10(22):4424-32. doi: 10.1039/c2ob25122a. Epub 2012 May 8.
PMID:22565504
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.
摘要
一种手性的四氢喹啉中间体（5）经八步反应，从单保护的乙二醇出发，通过钯催化的氮杂迈克尔加成反应诱导手性，可转化为三种戈里帕生物碱（安古斯特林、戈里帕碱和库斯帕林）。苄氧基的存在对合成的几个步骤都有深远的影响。
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