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Carbene‐Catalyzed Desymmetrization and Direct Construction of Arenes with All‐Carbon Quaternary Chiral Center
Author(s) -
Zhu Tingshun,
Liu Yingguo,
Smetankova Marie,
Zhuo Shitian,
Mou Chengli,
Chai Huifang,
Jin Zhichao,
Chi Yonggui Robin
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910183
Subject(s) - desymmetrization , enantioselective synthesis , carbene , indane , combinatorial chemistry , molecule , catalysis , chemistry , chirality (physics) , carbon fibers , quaternary carbon , asymmetric carbon , stereochemistry , organic chemistry , materials science , alkyl , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark , composite number , composite material
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.