Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore, 637371, Singapore.
Guiyang College of Traditional Chinese Medicine, Guizhou, P. R. China.
Angew Chem Int Ed Engl. 2019 Jan 8;58(2):477-481. doi: 10.1002/anie.201810879. Epub 2018 Dec 7.
A carbene and sulfinate co-catalyzed intermolecular Rauhut-Currier reaction between enals and nitrovinyl indoles is disclosed. The carbene catalyst activates the enal and the sulfinate co-catalyst activates the nitrovinyl indole. Both activation processes are realized via the formation of covalent bonds between the catalysts and substrates to generate catalyst-bound intermediates. The dual catalytic reaction affords azepino[1,2-a]indole products with excellent stereoselectivity. Our study demonstrates the unique involvement of sulfinate as an effective nucleophilic catalyst in activating electron-deficient alkenes for asymmetric reactions. This dual catalytic approach should also encourage future explorations of both sulfinate and carbene catalysts for new reactions.
一种卡宾和亚磺酸盐共同催化的烯醛和硝基亚乙烯基吲哚的分子间 Rauhut-Currier 反应被揭示。卡宾催化剂激活烯醛，亚磺酸盐共催化剂激活硝基亚乙烯基吲哚。两种活化过程都是通过催化剂和底物之间形成共价键来实现的，从而生成催化剂结合的中间体。双催化反应以优异的立体选择性得到氮杂[1,2-a]吲哚产物。我们的研究表明亚磺酸盐作为一种有效的亲核催化剂在活化缺电子烯烃进行不对称反应中的独特作用。这种双催化方法也应该鼓励未来对亚磺酸盐和卡宾催化剂在新反应中的探索。
