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

作　　者：Min Zhang Jun-Xin Wang Shun-Qin Chang Xiong-Li Liu Xiong Zuo Ying Zhou 

机构地区：[1]Guizhou Engineering Center for Innovative Traditional Chinese Medicine and Ethnic Medicine,Guizhou University,Guiyang 550025,China [2]College of Pharmaceutical Sciences,Guizhou University of Traditional Chinese Medicine,Guiyang 550025,China

出　　处：《Chinese Chemical Letters》2020年第2期381-385,共5页中国化学快报（英文版）

基　　金：financial support from the National Nature Science Foundation of China(Nos.81760625,81660576 and81560563);Projects of Guizhou Province(Nos.[2016]5623,JG[2016]06,[2019]1402,[2017]5609 and[2018]5781)。

摘　　要：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.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.

关 键 词：Chromone-oxindole SYNTHON Chromone-benzofuranone SYNTHON Inter-/intramolecular Michael CYCLOADDITION Bispiro[benzofuran-oxindole-chromanone] Bispirobenzofuranone 

分 类 号：O626[理学—有机化学] O621.251[理学—化学]