N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-ε-Lactones†
Prof. Dr. Hui Lv
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Key Laboratory for Green Chemical Process of Ministry of Education, School of material science and Engineering, Wuhan Institute of Technology, Wuhan, 430073 (China)
Search for more papers by this authorWen-Qiang Jia
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorLi-Hui Sun
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Song Ye
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)Search for more papers by this authorProf. Dr. Hui Lv
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Key Laboratory for Green Chemical Process of Ministry of Education, School of material science and Engineering, Wuhan Institute of Technology, Wuhan, 430073 (China)
Search for more papers by this authorWen-Qiang Jia
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorLi-Hui Sun
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Search for more papers by this authorCorresponding Author
Prof. Dr. Song Ye
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190 (China)Search for more papers by this authorFinancial support from the Ministry of Science and Technology of China (2011CB808600), National Natural Science Foundation of China (No. 21072195, 20932008), and the Chinese Academy of Sciences is gratefully acknowledged.
Graphical Abstract
Enantioselectivity through H bonding: An unprecedented [4+3] annulation of enals with o-quinone methides catalyzed by N-heterocyclic carbenes (NHCs) to give benzo-ε-lactones is described. High to excellent enantioselectivity was achieved by using a chiral triazolium NHC having a free OH group, which participates in a hydrogen-bonding interaction with the substrate.
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