Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine

被引：91

作者：

Chen, Si-Kai ^{[1
,2
]}

Ma, Wen-Qiang ^{[1
,2
]}

Yan, Zhi-Bo ^{[1
,2
]}

Zhang, Fu-Min ^{[1
,2
]}

Wang, Shao-Hua ^{[1
,2
]}

Tu, Yong-Qiang ^{[1
,2
,3
]}

Zhang, Xiao-Ming ^{[1
,2
]}

Tian, Jin-Miao ^{[3
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China

[2] Lanzhou Univ, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China

[3] Shanghai Jiao Tong Univ, Sch Chem & Chem Engn, Shanghai 200240, Peoples R China

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2018年 / 140卷 / 32期

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; PHASE-TRANSFER CATALYSTS; ALKALOID NATURAL-PRODUCTS; CONCISE TOTAL-SYNTHESIS; DIMERIC HPI ALKALOIDS; CYCLOTRYPTAMINE ALKALOIDS; MICHAEL ADDITION; HODGKINSINE-B; (+)-WIN 64821; 3-SUBSTITUTED OXINDOLES;

D O I：

10.1021/jacs.8b05386

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel chiral spirocyclic amide (SPA)-derived triazolium organocatalyst has been designed and demonstrated to effect asymmetric homo- and heterodialkylations of various bisoxindoles, enabling enantioselective construction of vicinal all-carbon quaternary stereocenters. These reactions feature excellent enantioand diastereoselectivities (up to 99% ee and >20:1 dr) as well as good to high yields (up to 89% over two steps). As an application of this methodology, the first asymmetric total synthesis of (-)-chimonanthidine has been achieved.

引用

页码：10099 / 10103

页数：5

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