Bis-Terminal Hydroxy Polyethers as All-Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications
作者:Ji Woong Lee、Hailong Yan、Hyeong Bin Jang、Hong Ki Kim、Sung-Woo Park、Sungyul Lee、Dae Yoon Chi、Choong Eui Song
DOI:10.1002/anie.200903903
日期:2009.9.28
Achiral polyether derivatives have been shown to dramatically accelerate SN2 reactions by the simultaneous activation of both the nucleophile (KF) and electrophile (sulfonate; see picture). By using chiral variants as catalysts, the desilylative kinetic resolution of the silyl ethers of racemic secondary alcohols has been achieved. Density functional calculations provide detailed insight into the modes
已显示非手性聚醚衍生物可通过亲核试剂(KF)和亲电试剂(磺酸盐;见图)的同时活化来显着加速S N 2反应。通过使用手性变体作为催化剂,已获得外消旋仲醇的甲硅烷基醚的脱甲硅烷基的动力学拆分。密度泛函计算可深入了解此类有机促进剂的作用方式。
A mild and efficient method for the selective deprotection of silyl ethers using KF in the presence of tetraethylene glycol
作者:Hailong Yan、Joong-Suk Oh、Choong Eui Song
DOI:10.1039/c1ob06300f
日期:——
efficient protocol for the deprotection of silylethers using KF in tetraethylene glycol is reported. A wide range of alcoholic silylethers can be selectively cleaved in high yield in the presence of certain acid- and base-labile functional groups. Moreover, the phenolic silylethers were cleaved exclusively, without affecting the alcoholic silylethers, at room temperature.