Carbene-catalyzed desymmetrization and direct construction of arenes with all-carbon quaternary chiral center

• Main Authors: Zhu, Tingshun, Liu, Yingguo, Smetankova, Marie, Zhuo, Shitian, Mou, Chengli, Chai, Huifang, Jin, Zhichao, Chi, Robin Yonggui
• Other Authors: School of Physical and Mathematical Sciences
• Format: Article
• Language: English
• Published: 2020
• Subjects: Science::Chemistry::Organic chemistry; Chirality; Cyclizations
• Online Access: https://hdl.handle.net/10356/137754
• Institution: Nanyang Technological University

Multisubstituted arenes such as indanes with attached all-carbon quaternary centers are unique scaffolds in synthetic functional molecules and sophisticated natural products. A key challenge in preparing such molecules lies in the enantioselective installation of the quaternary carbon centers. Conventional methods in this direction include asymmetric substitution reactions and substrate-controlled cyclization reactions. These reactions lead to poor stereoselectivities and/or require long and tedious synthetic steps. Disclosed here is a one-step organic catalytic strategy for enantioselective access to this class of molecules. The reaction involves an N-heterocyclic carbene catalyzed process for direct benzene construction, indane formation, remote-carbon desymmetrization, and excellent chirality control. This approach will enable the concise synthesis of arene-containing molecules, including those with complex structures and challenging chiral centers.