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Lewis Acid Catalyzed Cyclization Reactions of Ethenetricarboxylates via Intramolecular Hydride Transfer
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-06-21 00:00:00 , DOI: 10.1021/acs.joc.7b00895 Shoko Yamazaki 1 , Taku Naito 1 , Mamiko Niina 1 , Kiyomi Kakiuchi 2
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2017-06-21 00:00:00 , DOI: 10.1021/acs.joc.7b00895 Shoko Yamazaki 1 , Taku Naito 1 , Mamiko Niina 1 , Kiyomi Kakiuchi 2
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Catalytic cyclization of amides of ethenetricarboxylate bearing ether and acetal groups has been examined. The reaction of the amides bearing cyclic ether and acetal groups in the presence of Lewis acid such as Sc(OTf)3 gave spirocyclic piperidine derivatives as major products. The cyclized products may be formed via intramolecular hydride transfer. The reaction mechanism was examined by the DFT calculations. The scope and limitations of the hydride transfer/cyclization reactions of amides of ethenetricarboxylates was investigated, and morpholine formation by intramolecular oxy-Michael addition was also found.
中文翻译：
路易斯酸通过分子内氢化物转移催化乙烯醚羧酸酯的环化反应
已经研究了带有醚和缩醛基团的三羧酸乙烯酯的酰胺的催化环化。在路易斯酸如Sc（OTf）3的存在下，带有环醚和缩醛基的酰胺的反应得到螺环哌啶衍生物作为主要产物。环化产物可以通过分子内氢化物转移形成。通过DFT计算检查了反应机理。研究了三羧酸乙烯酯的酰胺的氢化物转移/环化反应的范围和局限性，还发现了通过分子内氧-迈克尔加成形成吗啉的现象。
更新日期：2017-06-28
中文翻译：
路易斯酸通过分子内氢化物转移催化乙烯醚羧酸酯的环化反应
已经研究了带有醚和缩醛基团的三羧酸乙烯酯的酰胺的催化环化。在路易斯酸如Sc（OTf）3的存在下，带有环醚和缩醛基的酰胺的反应得到螺环哌啶衍生物作为主要产物。环化产物可以通过分子内氢化物转移形成。通过DFT计算检查了反应机理。研究了三羧酸乙烯酯的酰胺的氢化物转移/环化反应的范围和局限性，还发现了通过分子内氧-迈克尔加成形成吗啉的现象。
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