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Catalytic Enantioselective Double Carbopalladation/C−H Functionalization with Statistical Amplification of Product Enantiopurity: A Convertible Linker Approach
Author(s) -
Tong Shuo,
Limouni Aurore,
Wang Qian,
Wang MeiXiang,
Zhu Jieping
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201709133
Subject(s) - enantioselective synthesis , chemistry , dimer , alkylation , linker , catalysis , combinatorial chemistry , stereochemistry , organic chemistry , computer science , operating system
Combining a catalytic enantioselective reaction with dimerization in a single operation is an efficient way to upgrade the enantiomeric excesses ( ee ) of the product. Palladium‐catalyzed reaction of N ‐(2‐iodophenyl)‐ N ‐methyl methacrylamide derivatives with oxadiazole afforded, by a double enantioselective carbopalladation/intermolecular heteroarene C−H alkylation sequence, homodimers in good yields with excellent ee values. The dimer was subsequently elaborated to the monomer in which the linker (oxadiazole) was incorporated into the target product.