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Enantioselective Palladium-Catalyzed Domino Carbonylative Heck Esterification of o‑Iodoalkenylbenzenes with Arylboronic Acids

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posted on 2023-11-03, 15:39 authored by Yao-Du Zhang, Ming Chen, Yang Li, Bo-Wen Liu, Zhi-Hui Ren, Zheng-Hui Guan
The current investigation presents an innovative palladium-catalyzed asymmetric carbonylative Heck esterification method. This approach facilitates the efficient synthesis of various chiral γ-ketoacid esters by utilizing o-alkenyliodobenzenes and arylboronic acids as primary substrates. This reaction achieves the creation of three carbon–carbon bonds, two carbon–oxygen bonds, and the establishment of a quaternary carbon center within a single step. The α-chiral γ-ketoacid esters were obtained in yields ranging from good to high yields, displaying enantiomeric excesses (ee’s) levels up to 92% under mild reaction conditions.

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