3 years ago

Catalytic Enantioselective Double Carbopalladation/C−H Functionalization with Statistical Amplification of Product Enantiopurity: A Convertible Linker Approach

Catalytic Enantioselective Double Carbopalladation/C−H Functionalization with Statistical Amplification of Product Enantiopurity: A Convertible Linker Approach
Qian Wang, Jieping Zhu, Shuo Tong, Mei-Xiang Wang, Aurore Limouni
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. Duplicates: A new dimension of the Horeau duplication principle is demonstrated in the palladium-catalyzed reaction of N-(2-iodophenyl)-N-methyl methacrylamide derivatives with oxadiazole to afford homodimers in good yields with excellent enantiomeric excesses (ee). The dimer was subsequently converted into a structurally elaborated monomer in which the linker (oxadiazole) was incorporated into the target product.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201709133

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