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Bis‐Terminal Hydroxy Polyethers as All‐Purpose, Multifunctional Organic Promoters: A Mechanistic Investigation and Applications
Author(s) -
Lee Ji Woong,
Yan Hailong,
Jang Hyeong Bin,
Kim Hong Ki,
Park SungWoo,
Lee Sungyul,
Chi Dae Yoon,
Song Choong Eui
Publication year - 2009
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200903903
Subject(s) - sn2 reaction , electrophile , nucleophile , silylation , chemistry , sulfonate , catalysis , organic synthesis , organic chemistry , combinatorial chemistry , computer science , sodium
Achiral polyether derivatives have been shown to dramatically accelerate S N 2 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 of action of this type of organic promoter.