Concise Report
Enantioselective Synthesis of Planar/Multiple Chiral [n]Cyclophanes through Asymmetric Allylation
Ziyang Wang,
Xin-Xin Zhang,
Yidan Sun,
Hanliang Zheng,
Xin Li,
Ziyang Wang
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorXin-Xin Zhang
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorYidan Sun
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Hanliang Zheng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang, 321004 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Xin Li
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
E-mail: [email protected]; [email protected]Search for more papers by this authorZiyang Wang,
Xin-Xin Zhang,
Yidan Sun,
Hanliang Zheng,
Xin Li,
Ziyang Wang
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorXin-Xin Zhang
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorYidan Sun
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Search for more papers by this authorCorresponding Author
Hanliang Zheng
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, College of Chemistry and Materials Science, Zhejiang Normal University, Jinhua, Zhejiang, 321004 China
E-mail: [email protected]; [email protected]Search for more papers by this authorCorresponding Author
Xin Li
State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin, 300071 China
Haihe Laboratory of Sustainable Chemical Transformations, Tianjin, 300192 China
E-mail: [email protected]; [email protected]Search for more papers by this authorComprehensive Summary
Planar-chiral cyclophanes with carbon-centered chirality are important targets in natural products and pharmaceuticals. However, synthesizing such planar chiral cyclophanes with two stereogenic elements via a one-step asymmetric reaction remains a formidable challenge. Herein, we present an efficient kinetic resolution method for synthesizing planar-chiral [n]cyclophanes with carbon-centered chirality. This is achieved through the enantioselective allylation of racemic aldehyde [n]cyclophanes catalyzed by Bi(OAc)3 and chiral phosphoric acid. The reaction delivers planar-chiral [n]cyclophanes and multiple chiral [n]cyclophanes with high yields and excellent enantioselectivities, showcasing remarkable kinetic resolution efficiency (s factor up to 292). The broad substrate scope, scalability, and potential for derivatization highlight the value of this methodology. DFT calculations have also been performed to provide insights into the origin of the experimentally observed diastereo- and enantioselectivity for this reaction.
Supporting Information
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Appendix S1: Supporting Information |
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