Access to all-carbon spirocycles through a carbene and thiourea cocatalytic desymmetrization cascade reaction

• Main Authors: Zhuo, Shitian, Zhu, Tingshun, Zhou, Liejin, Mou, Chengli, Chai, Huifang, Lu, Yunpeng, Pan, Lutai, Jin, Zhichao, Chi, Robin Yonggui
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry::Organic chemistry; Desymmetrization; Dual Catalysis
• Online Access: https://hdl.handle.net/10356/137748
• Institution: Nanyang Technological University

A new catalytic approach for rapid asymmetric access to spirocycles is disclosed. The reaction involves a carbene- and thiourea-cocatalyzed desymmetrization process with the simultaneous installation of a spirocyclic core. The use of a thiourea cocatalyst is critical to turn on this reaction, as no product was formed in the absence of a thiourea. Our study constitutes the first success in the carbene-catalyzed enantioselective synthesis of all-carbon spirocycles. The reaction products can be readily transformed into sophisticated multicyclic molecules and chiral ligands.