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Synthesis of dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline through Cu(OTf)2-catalyzed reactions of N-acyliminium ions with ynamides
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2021-02-04 , DOI: 10.1016/j.tetlet.2021.152873
Rui-Jun Ma , Wen-Ke Xu , Jian-Ting Sun , Ling Chen , Chang-Mei Si , Bang-Guo Wei

An efficient approach to access functionalized dihydro-[1,3]oxazino[4,3-a] isoindole and tetrahydroisoquinoline skeletons has been developed through the addition-cyclization process of ynamides 8 with N-acyliminium ions generated from N,O-acetals 6,7. The reactions were conducted under the catalysis of Cu(OTf)2, and a number of functionalized dihydro-[1,3]oxazino[4,3-a] isoindoles 9a-9y and tetrahydroisoquinolines 10a-10g, 11a-11p were generated in 48–98% yields. When chiral ynamides 8n-8u were used, optically pure products 11a-11p could be obtained with good to excellent yields and diastereoselectivities.



中文翻译:

Cu(OTf)2催化N-酰基亚胺离子与酰胺的反应合成二氢-[1,3]恶嗪基[4,3-a]异吲哚和四氢异喹啉

通过使用由N,O-缩醛6生成的N-酰亚胺离子对酰胺8进行加成环化工艺,已经开发出一种有效的方法来访问官能化的二氢-[1,3]恶嗪[4,3-a]异吲哚和四氢异喹啉骨架。,7。反应在Cu(OTf)2的催化下进行,并在其中生成了许多官能化的二氢-[1,3]恶嗪基[4,3-a]异吲哚9a-9y和四氢异喹啉10a-10g,11a-11p。 48–98%的产量。当使用手性乙酰胺8n-8u时,可以获得具有良好或优异的产率和非对映选择性的光学纯产物11a-11p

更新日期:2021-03-04
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