Chiral Tertiary Amine Catalyzed Asymmetric [4 + 2] Cyclization of 3-Aroylcoumarines with 2,3-Butadienoate |
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| Authors: | Jun-Lin Li Xiao-Hui Wang Jun-Chao Sun Yi-Yuan Peng Cong-Bin Ji Xing-Ping Zeng |
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| Affiliation: | 1.Key Laboratory of Small Functional Organic Molecule, Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330022, China; (J.-L.L.); (X.-H.W.); (J.-C.S.); (Y.-Y.P.);2.Jiangxi Provincial Research of Targeting Pharmaceutical Engineering Technology, Shangrao Normal University, Shangrao 334001, China; |
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| Abstract: | 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. |
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| Keywords: | coumarins, dihydrocoumarin-fused dihydropyranones, 3-aroylcoumarines, benzyl 2,3-butadienoate, 6’ -(4-biphenyl)-β -iso-cinchonine |
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