Cooperative Diarylborinic Acid/Chloride-Catalyzed Formal SNi Reaction of cis-4-Hydroxymethyl-1,2-Cyclopentene Oxides

作者：Shan-Shan Xun, Gao‐Wei Wang, Sheng-Mei Lu, Yong‐Gui Zhou · 发表于：Organic Letters · 年份：2024 · DOI：10.1021/acs.orglett.4c03077 · 被引用次数：5 · 研究领域：Carbon dioxide utilization in catalysis、Chemical Synthesis and Reactions、Asymmetric Hydrogenation and Catalysis

A catalytic formal S N i reaction was designed to achieve stereoretentive products for cis -4-hydroxymethyl-1,2-cyclopentene oxides by using diarylborinic acid as a dual role catalyst and chloride as a catalytic transient nucleophile through a double-displacement mechanism. This reaction offers the advantages of a low catalyst loading of 0.1 mol % and wide substrate scope, even including N -substituents. The use of chiral boron acid as a catalyst for this reaction was also attempted.