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Palladium-Catalyzed Asymmetric Domino Heck/Carbocyclization/Suzuki Reaction: A Dearomatization of Nonactivated Naphthalenes
CCS Chemistry ( IF 11.2 ) Pub Date : 2021-01-19 , DOI: 10.31635/ccschem.020.202000596
Ming Chen 1 , Xucai Wang 1 , Zhi-Hui Ren 1 , Zheng-Hui Guan 1
Affiliation  

Herein, we report a novel palladium (Pd)-catalyzed asymmetric domino Heck/carbocyclization/Suzuki reaction of N-(2-bromoaryl)-2-naphthylacrylamides. The reaction involves a novel and enantioselective dearomative 1,2-insertion of the naphthalene group, thus providing a unique dearomatization strategy of nonactivated naphthalenes. A new phosphoramidite ligand L12, which displayed excellent reactivity and enantioselectivity in the reaction, has been developed. The reaction employs readily available starting materials, and provides straightforward access to a diverse array of spirooxindoles bearing three stereogenic centers in high yields under mild conditions.



中文翻译:

钯催化的不对称多米诺骨节/碳环化/铃木反应:非活化萘的脱芳香化作用

在这里,我们报告了新型钯(Pd)催化的N-(2-溴芳基)-2-萘丙烯酰胺的不对称多米诺Heck /碳环化/ Suzuki反应。该反应涉及萘基团的新颖和对映选择性脱芳香基的1,2-插入,因此提供了非活化萘的独特的脱芳香化策略。一种新的亚磷酰胺配体 L12已经开发出在反应中显示出优异的反应性和对映选择性的化合物。该反应采用容易获得的起始原料,并在温和条件下以高收率直接获得具有3个立体异构中心的多种螺硫辛醇。

更新日期:2021-01-19
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