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Brønsted Acid Catalyzed Asymmetric S N 2‐Type O‐Alkylations
Author(s) -
Čorić Ilija,
Kim Ji Hye,
Vlaar Tjøstil,
Patil Mahendra,
Thiel Walter,
List Benjamin
Publication year - 2013
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.201209983
Subject(s) - bridging (networking) , sn2 reaction , intramolecular force , alkylation , nucleophile , chemistry , computer science , catalysis , brønsted–lowry acid–base theory , combinatorial chemistry , stereochemistry , organic chemistry , computer network
Bridging the gap : Brønsted acids catalyze an intramolecular S N 2‐type alkylation of alcohols with ethers by bridging a pentacoordinate transition state, thus simultaneously activating both the leaving group and nucleophile (see scheme). Density functional calculations provide detailed insight into the course of the reaction and the transition‐state structure.