Concise Report
Enantioselective Construction of Polycyclic Chromanes through Organocatalytic Sequential Quintuple Reaction via One-Pot Step-Wise Procedure
Jie Wang,
Hang Qin,
Ya-Li Song,
Fei Cao,
Zhi-Hao You,
Jie Wang
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Search for more papers by this authorHang Qin
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Search for more papers by this authorYa-Li Song
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Baoding, Hebei, 071002 China
Search for more papers by this authorFei Cao
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Baoding, Hebei, 071002 China
Search for more papers by this authorCorresponding Author
Zhi-Hao You
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Baoding, Hebei, 071002 China
E-mail: [email protected]Search for more papers by this authorJie Wang,
Hang Qin,
Ya-Li Song,
Fei Cao,
Zhi-Hao You,
Jie Wang
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Search for more papers by this authorHang Qin
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Search for more papers by this authorYa-Li Song
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Baoding, Hebei, 071002 China
Search for more papers by this authorFei Cao
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Baoding, Hebei, 071002 China
Search for more papers by this authorCorresponding Author
Zhi-Hao You
Key Laboratory of Pharmaceutical Quality Control of Hebei Province, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002 China
Key Laboratory of Medicinal Chemistry and Molecular Diagnosis of the Ministry of Education, Baoding, Hebei, 071002 China
E-mail: [email protected]Search for more papers by this authorFirst published: 14 May 2024
Comprehensive Summary
An efficient and highly stereoselective synthetic method to access polycyclic chromanes has been achieved through organocatalyzed one-pot step-wise reactions involving 2-hydroxycinnamaldehydes, 2-aminochalcones, and malononitrile as substrates. The reactions underwent a quintuple process by aza-Michael/Michael/Knoevenagel/oxa-Michael/aldol-type reaction in sequence to give products bearing 3 new generated rings and 5 chiral centers in moderate to quantitative yields with excellent stereoselectivities. A novel retro-reaction mechanism was discovered in the synthetic transformations of products.
Supporting Information
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Appendix S1: Supporting Information |
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