Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid
Enantioselective Synthesis of 1-Substituted 1,2,3,4-Tetrahydroisoquinolines through 1,3-Dipolar Cycloaddition by a Chiral Phosphoric Acid
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DOI：
10.1055/s-0039-1690108
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发表时间：
2019-06
期刊：
影响因子：
2
通讯作者：
Yuan Jin;Yasuhiro Honma;Hisashi Morita;Masamichi Miyagawa;T. Akiyama
中科院分区：
文献类型：
--
作者：
Yuan Jin;Yasuhiro Honma;Hisashi Morita;Masamichi Miyagawa;T. Akiyama
摘要 描述了一种不对称合成 1-取代 1,2,3,4-四氢异喹啉的新方法，该方法基于硝酮和乙烯基醚在手性磷酸存在下的对映选择性 1,3-偶极环加成反应，以高收率和高对映选择性生成手性四氢异喹啉。硝酮和手性磷酸混合物的 1H 和 31P NMR 分析表明形成了 1:1 络合物。
Abstract A new approach is described for the asymmetric synthesis of 1-substituted 1,2,3,4-tetrahydroisoquinolines that is based on the enantioselective 1,3-dipolar cycloaddition reaction of a nitrone and a vinyl ether in the presence of a chiral phosphoric acid that gives the chiral tetrahydroisoquinolines in high yields and with high enantioselectivities. 1H and 31P NMR analyses of the mixture of nitrone and chiral phosphoric acid suggest the formation of a 1:1 complex.