Citation: Zhang Min, Wang Jun-Xin, Chang Shun-Qin, Liu Xiong-Li, Zuo Xiong, Zhou Ying. Highly efficient enantioselective synthesis of bispiro [benzofuran-oxindole/benzofuran-chromanone]s through organocatalytic inter-/intramolecular Michael cycloaddition[J]. Chinese Chemical Letters, ;2020, 31(2): 381-385. doi: 10.1016/j.cclet.2019.06.015 shu

Highly efficient enantioselective synthesis of bispiro [benzofuran-oxindole/benzofuran-chromanone]s through organocatalytic inter-/intramolecular Michael cycloaddition

a.
Guizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine, Guizhou University, Guiyang 550025, China
b.
College of Pharmaceutical Sciences, Guizhou University of Traditional Chinese Medicine, Guiyang 550025, China

xlliu1@gzu.edu.cn

Received Date: 9 May 2019
Revised Date: 30 May 2019
Accepted Date: 6 June 2019
Available Online: 7 June 2019

Figures(7)

A quinine-derived thiourea-catalyzed inter-/intramolecular Michael cycloaddition of chromoneoxindole/benzofuranone synthons with 3-substituted methylenebenzofuranones has been established, which constructed enantiomerically pure bispiro[benzofuran-oxindole/benzofuran-chromanone]s bearing five consecutive stereocenters including two spiro quaternary carton centers in good yields (up to 93%) with high diastereoselectivities (up to >20:1 dr) and good enantioselectivities (up to >99% ee). Moreover, this is the first example of bifunctional chromone-benzofuranone synthon directed organocatalytic tandem reaction, and also the first example of the bispiro[benzofuran-oxindole] and bispirobenzofuranone, potentially useful in medicinal chemistry.
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