Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstr. 21, 79104 Freiburg, Germany.
Org Lett. 2015 May 15;17(10):2478-81. doi: 10.1021/acs.orglett.5b00987. Epub 2015 Apr 30.
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.
本文介绍了一种 3,4-二氢异喹啉的催化还原 C1-酰化反应，该反应可直接得到 1,1-二取代的四氢异喹啉。该反应是一种钛（III）催化的还原反转过程，其中腈作为有效的酰化试剂。该方法具有高度的化学和区域选择性，并在 20 个实例中得到了证明。它非常适合于官能化的四氢异喹啉产物的大规模合成，这在（±）-3-去甲氧基麦角新碱的六步合成立方中得到了例证。
