Solvent-Controlled Enantiodivergent Construction of P(V)-Stereogenic Molecules via Palladium-Catalyzed Annulation of Prochiral N-Aryl Phosphonamides with Aromatic Iodides
Qingyu Tian
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorJin Ge
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorYaopeng Liu
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorXi Wu
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorZhenghao Li
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Guolin Cheng
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University, Nanchang, 330022 China
Search for more papers by this authorQingyu Tian
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorJin Ge
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorYaopeng Liu
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorXi Wu
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorZhenghao Li
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Guolin Cheng
Xiamen Key Laboratory of Optoelectronic Materials and Advanced Manufacturing, College of Materials Science and Engineering, Huaqiao University, Xiamen, 361021 China
Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University, Nanchang, 330022 China
Search for more papers by this authorGraphical Abstract
A new strategy for enantiodivergent accessing P(V)-stereogenic molecules via palladium/norbornene cooperative catalysis was established. The enantioselectivity of this protocol was tuned by the polarity of the solvent, thus providing both enantiomers of the P(V)-stereogenic molecules using a single chiral norbornene catalyst.
Abstract
In this work, we describe an efficient and modular method for enantiodivergent accessing P(V)-stereogenic molecules by utilizing the catalytic atroposelective Catellani-type C−H arylation/desymmetric intramolecular N-arylation cascade reaction. The enantioselectivity of this protocol was proved to be tuned by the polarity of the solvent, thus providing a wide range of both chiral P(V)-stereogenic enantiomers in moderate to good yields with good to excellent enantiomeric excesses. Noteworthy is that the strategy developed herein represents an unprecedented example of solvent-dictated inversion of the enantioselectivity of P(V)-stereogenic compounds.
Conflict of Interests
The authors declare no conflict of interest.
Open Research
Data Availability Statement
Deposition numbers 2335991 (4 x), contain the supplementary crystallographic data for this paper. These data are provided free of charge by the joint Cambridge Crystallographic Data Centre and Fachinformationszentrum Karlsruhe Access Structures service.
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