Organocatalytic Atroposelective Hydroselenation of Alkynes To Access Axially Chiral Vinyl Selenides

作者：Yi-Xin Wang, Jing-Run Wang, Chen Cui, Zhen Wang, Lu Yu, Xiao‐Hui Yang · 发表于：ACS Catalysis · 年份：2025 · DOI：10.1021/acscatal.4c07281 · 被引用次数：10 · 研究领域：Axial and Atropisomeric Chirality Synthesis、Molecular spectroscopy and chirality、Asymmetric Synthesis and Catalysis

While the catalytic asymmetric hydrofunctionalization of unsaturated hydrocarbons has been widely investigated, the asymmetric hydrofunctionalization of alkynes, which yields atropoisomeric products, remains significantly underexplored. Herein, we showcase an unprecedented organocatalytic atroposelective hydroselenation of alkynes with selenols, leading to the formation of axially chiral vinyl selenides. This organocatalytic, atom-economic process occurs under mild conditions and exhibits high enantio-, regio-, and E -stereoselectivity, despite the relatively low racemization barrier (Δ G ‡ = ∼27 kcal/mol) of the formed axially chiral vinyl selenides. Insights from detailed Density Functional Theory (DFT) studies elucidate the origins of these high selectivities.