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Updated: Sep 13, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Chiral Transient Directing Group Enabled Palladium-Catalyzed Atroposelective C-H Vinylation of Biaryl Aldehydes with
Vadivel Arjun1, Karan Kaushik1, Masilamani Jeganmohan1
1Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600036, India.
Abstract:
Herein, we report a palladium-catalyzed atroposelective C-H vinylation approach for the construction of axially chiral biaryls featuring vinyl substituents, enabled by a chiral transient directing group. Notably, this transformation proceeds efficiently with vinyl silane as the vinyl source, without requiring any external fluoride additives. This protocol exhibits a broad substrate scope, efficiently transforming diverse biaryl-2-aldehydes into atroposelective vinylated products in excellent yields with high enantioselectivities up to >99.9% ee. Additionally, mechanistic studies were performed to validate the proposed reaction pathway, and post-synthetic modifications demonstrate the synthetic utility of the methodology.
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