Synthesis of Enantioenriched 1,2-cis Disubstituted Cycloalkanes by Convergent NiH Catalysis |
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Authors: | Changpeng Chen Wenqing Guo Deyong Qiao Prof Shaolin Zhu |
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Institution: | State Key Laboratory of Coordination Chemistry, Jiangsu Key Laboratory of Advanced Organic Materials, Chemistry and Biomedicine Innovation Center (ChemBIC), School of Chemistry and Chemical Engineering, Nanjing University, 210093 Nanjing, China |
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Abstract: | Enantioenriched multi-substituted cycloalkanes constitute an essential class of compounds in pharmaceuticals, natural products and agrochemicals. Here we report an NiH-catalyzed asymmetric migratory hydroalkylation process for the efficient and selective construction of such compounds. Through a dynamic kinetic asymmetric transformation (DYKAT), easily accessible racemic and isomeric mixtures of cycloalkenes could be directly utilized as starting materials, convergently producing thermo-dynamically disfavored chiral 1,2-cis disubstituted cycloalkanes bearing vicinal stereocenters with high levels of regio-, diastereo- and enantioselectivity. In addition, prochiral cyclic alkenes can be also employed, and deliver chiral 1,2-cis disubstituted cycloalkanes through desymmetrization process. |
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Keywords: | Alkenes Alkylation Asymmetric Catalysis Isomerization Nickel |
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