Chiral Tertiary Amine Catalyzed Asymmetric [4 + 2] Cyclization of 3-Aroylcoumarines with 2,3-Butadienoate
Jun-Lin Li,
Xiao-Hui Wang,
Jun-Chao Sun,
Yi-Yuan Peng,
Cong-Bin Ji,
Xing-Ping Zeng
Affiliations
Jun-Lin Li
Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
Xiao-Hui Wang
Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
Jun-Chao Sun
Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
Yi-Yuan Peng
Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
Cong-Bin Ji
Jiangxi Provincial Research of Targeting Pharmaceutical Engineering Technology, Shangrao Normal University, Shangrao 334001, China
Xing-Ping Zeng
Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China
Coumarins and 2H-pyran derivatives are among the most commonly found structural units in natural products. Therefore, the introduction of 2H-pyran moiety into the coumarin structural unit, i.e., dihydrocoumarin-fused dihydropyranones, is a potentially successful route for the identification of novel bioactive structures, and the synthesis of these structures has attracted continuing research interest. Herein, a chiral tertiary amine catalyzed [4 + 2] cyclization of 3-aroylcoumarines with benzyl 2,3-butadienoate was reported. In the presence of Kumar’s 6’-(4-biphenyl)-β-iso-cinchonine, the desired dihydrocoumarin-fused dihydropyranone products could be obtained in up to 97% yield and 90% ee values.
