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B(C6F5)3-catalyzed cyclopropanation of 3-alkenyl-oxindoles with diazomethanes
Chemical Communications ( IF 4.9 ) Pub Date : 2023-01-18 , DOI: 10.1039/d2cc06744g
Lei Xiao 1 , Lvnan Jin 1 , Yunbo Zhao 1 , Jing Guo 1 , Douglas W Stephan 1, 2
Affiliation  

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.

中文翻译:

B(C6F5)3-催化 3-烯基-羟吲哚与重氮甲烷的环丙烷化反应

Spirocyclopropane-oxindoles 是生物活性化合物中的关键基序,是多功能的合成中间体。在此,我们报告了3-烯基羟吲哚与重氮甲烷的无金属 B(C 6 F 5 ) 3催化环丙烷化反应。这提供了螺环丙烷-羟吲哚衍生物的 25 种变体。这些螺环丙烷-羟吲哚产物在温和的反应条件下以良好至优异的产率(高达 99%)和高非对映选择性(高达 20:1 dr)获得,并且可以在克规模上进行。
更新日期:2023-01-18
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