State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032 (P.R. China).
Angew Chem Int Ed Engl. 2014 Dec 1;53(49):13532-5. doi: 10.1002/anie.201406959. Epub 2014 Oct 6.
A Sc(OTf)3 -catalyzed cascade Prins-type cyclization reaction of o-alkynylanilines, bearing a hydroxy or amine functionality, with aldehydes affords 1,2-dihydroquinoline derivatives having an extra fused ring efficiently under mild reaction conditions. It is interesting to observe the reversed reactivity in the highly selective formation of 1,2-dihydroquinoline derivatives instead of the formation of the usually favored indole derivatives.
Sc(OTf)3 催化的邻炔基苯胺(带有羟基或氨基官能团)与醛的 Prins 型环化反应,在温和的反应条件下有效地得到具有额外稠合环的 1,2-二氢喹啉衍生物。有趣的是,观察到了相反的反应性,即高度选择性地形成 1,2-二氢喹啉衍生物而不是通常更有利的吲哚衍生物。