Citation: Xiao Yuanyuan, Wang Youming, Zhou Zhenghong. Asymmetric Synthesis of Novel Fused Polycyclic 3, 4-Dihydro-pyrano[4, 3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation[J]. Chinese Journal of Organic Chemistry, ;2019, 39(8): 2203-2210. doi: 10.6023/cjoc201703070 shu

Asymmetric Synthesis of Novel Fused Polycyclic 3, 4-Dihydro-pyrano[4, 3-b]pyran-5(2H)-ones via an Organocatalyzed Formal[3+3] Annulation

Institute and State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University, Tianjin 300071

Corresponding author: Zhou Zhenghong, z.h.zhou@nankai.edu.cn
Received Date: 29 March 2019
Revised Date: 10 May 2019
Available Online: 28 August 2019

Figures(3)

A chiral bifunctional squaramide catalyzed enantioselective formal[3+3] annulation of 4-hydroxy-2H-pyrano[2', 3':4, 5]pyrano[2, 3-c]pyrazole-2, 5(7H)-diones and (E)-2-nitroallyl acetates has been developed, which provides an efficient approach to stereocontrolled construction of fused polycyclic 3, 4-dihydropyrano[4, 3-b]pyran-5(2H)-one scaffold. Under the catalysis of a bifunctional squaramide derived from (1R, 2R)-1, 2-diphenylethane-1, 2-diamine, a wide range of novel fused polycyclic 3, 4-dihydropyrano[4, 3-b]pyran-5(2H)-one derivatives with two adjacent stereogenic centers are obtained in acceptable yields with high anti-selectivity and moderate to excellent enantioselectivity. Representative transformation of the annulation product to other synthetic valuable compound is achieved without any loss of stereochemical integrity.
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