Palladium-Catalyzed Transient Chirality Transfer and Atroposelective C-H Functionalization to Access Quaternary Stereocenters
Lu-Lu Han
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorCorresponding Author
Dr. Yu-Ming Cui
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorQin Yang
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorLi-Lei Fang
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorCorresponding Author
Prof. Dr. Li-Wen Xu
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorLu-Lu Han
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorCorresponding Author
Dr. Yu-Ming Cui
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorQin Yang
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorLi-Lei Fang
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorCorresponding Author
Prof. Dr. Li-Wen Xu
Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Key Laboratory of Organosilicon Material Technology of Zhejiang Province, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, Zhejiang, 311121 People's Republic of China
Search for more papers by this authorAbstract
Although palladium-catalyzed asymmetric C−H functionalization and Heck reactions represents one of the most important synthetic strategies for the construction of quaternary stereocenters, developing the enantioselective version of PdII-catalyzed carbopalladation-initiated cascade reactions still remains a formidable challenge. Herein, an unprecedent enantioselective [3+2] annulation of oxime ethers and alkynes has been developed, providing both spiro and nonspiro indenes bearing all-carbon quaternary stereocenters in good yields (up to 98 %) with excellent enantioselectivities (up to >99 % ee). This annulation is accomplished by merging the PdII-catalyzed atroposelective C−H activation/double carbopalladation and the transient axial-to-central chirality transfer process, constituting the first successful example of catalytic chirality transfer strategy involving axially chiral styrene intermediate.
Open Research
Data Availability Statement
The data that support the findings of this study are available in the Supporting Information of this article.
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