Sulfinate and carbene co-catalyzed Rauhut-Currier reaction for enantioselective access to azepino[1,2-a]indoles

• Main Authors: Wu, Xingxing, Zhou, Liejin, Maiti, Rakesh, Mou, Chengli, Pan, Lutai, Chi, Robin Yonggui
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry::Organic chemistry; Cooperative Catalysis; Indoles
• Online Access: https://hdl.handle.net/10356/137927
• Institution: Nanyang Technological University

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.