A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines
A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines
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DOI：
10.1021/acs.orglett.5b00987
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发表时间：
2015-05-15
期刊：
影响因子：
5.2
通讯作者：
Streuff, Jan
中科院分区：
文献类型：
--
作者：
Hieu-Trinh Luu;Wiesler, Stefan;Streuff, Jan
提出了3,4-二氢异喹啉的催化还原c1 -酰化反应，直接得到1,1-二取代的四氢异喹啉。该反应是钛（III）催化的还原混合反应，其中腈作为有效的酰化剂。该方法具有高度的化学选择性和区域选择性，并通过20个实例进行了验证。它非常适合大规模合成功能化四氢异喹啉产物，例如(+/-)-3-去甲氧基赤藓苷酮的六步合成。
A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in the form of a six-step synthesis of (+/-)-3-demethoxyerythratidinone.