Modular Access to Chiral 1, 3-Substituted Fragments via Nickel-Catalyzed Arylboration Reaction
Yang Bao , Tong Yao , Weiyu Kong , Yangyang Li , Ying Fu , Dong Wu , Guoyin Yin
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (3) : 261 -267.
Modular Access to Chiral 1, 3-Substituted Fragments via Nickel-Catalyzed Arylboration Reaction
Chiral 1, 3-substituted fragments are ubiquitous in pharmaceutical molecules and natural products, prompting the development of numerous methods to access these structures. Nonetheless, devising synthetic routes for complex chiral architectures in practical applications typically demands years of expertise. Herein, we developed a nickel-catalyzed enantioselective migratory arylboration reaction of allylboronic esters using a chiral 1, 2-diamine ligand, yielding a range of chiral 1, 3-bis(boronates) with high enantioselectivity. The protocol is characterized by its use of commercially available substrates, mild reaction conditions, user-friendly procedures, and a broad substrate compatibility. Moreover, we demonstrate the practicality and application potential of this reaction by synthesizing several key drug intermediates.
Alkenes / Nickel / Chiral 1, 3-bis(boronates) / Chain-walking / Carboboration / Enantioselectivity
2024 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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