B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes

被引：19

作者：

Xiao, Lei ^{[1
]}

Jin, Lvnan ^{[1
]}

Zhao, Yunbo ^{[1
]}

Guo, Jing ^{[1
]}

Stephan, Douglas W. W. ^{[1
,2
]}

机构：

[1] Ningbo Univ, Inst Drug Discovery Technol, Ningbo, Zhejiang, Peoples R China

[2] Univ Toronto, Dept Chem, 80 St George St, Toronto, ON M5S 3H6, Canada

来源：

CHEMICAL COMMUNICATIONS | 2023年 / 59卷 / 13期

关键词：

REVERSE-TRANSCRIPTASE INHIBITORS; H BOND FUNCTIONALIZATION; DIAZO-COMPOUNDS; ASYMMETRIC CYCLOPROPANATION; BIOLOGICAL EVALUATIONS; INSERTION; PHENOLS; DIAZOOXINDOLES; OXINDOLES; DESIGN;

D O I：

10.1039/d2cc06744g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Spirocyclopropane-oxindoles are key motifs in biologically active compounds and are versatile synthetic intermediates. Herein, we report a metal-free, B(C6F5)(3) catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes. This provides 25 variants of spirocyclopropane-oxindole derivatives. These spirocyclopropane-oxindole products were obtained in good to excellent yields (up to 99%) and high diastereoselectivities (up to 20 : 1 d.r.) under mild reaction conditions and could be performed on a gram scale.

引用

页码：1833 / 1836

页数：4

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