Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (8): 2203-2210.DOI: 10.6023/cjoc201703070 Previous Articles     Next Articles

Special Issue: 陈茹玉先生诞辰100周年

Articles

有机催化不对称[3+3]环化合成新型光学活性稠合多环3,4-二氢吡喃并[4,3-b]吡喃-5-(2H)-酮

肖园园, 王有名, 周正洪   

  1. 南开大学化学学院 元素有机化学国家重点实验室 天津 300071
  • 收稿日期:2019-03-29 修回日期:2019-05-10 出版日期:2019-08-25 发布日期:2019-05-28
  • 通讯作者: 周正洪 E-mail:z.h.zhou@nankai.edu.cn

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

Xiao Yuanyuan, Wang Youming, Zhou Zhenghong   

  1. 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
  • Received:2019-03-29 Revised:2019-05-10 Online:2019-08-25 Published:2019-05-28
  • Contact: 10.6023/cjoc201703070 E-mail:z.h.zhou@nankai.edu.cn

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.

Key words: asymmetric synthesis, fused polycyclic 3,4-dihydropyrano[4,3-b]pyran-5(2H)-one, 4-hydroxy-2H-pyrano[2',3':4,5]pyrano[2,3-c]pyrazole-2,5(7H)-dione, (E)-2-nitroallyl acetate, organocatalysis