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Lithiation of a Silyl Ether: Formation of an ortho ‐Fries Hydroxyketone
Author(s) -
Lo HongJay,
Lin ChinYin,
Tseng MeiChun,
Chein RongJie
Publication year - 2014
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.201404495
Subject(s) - lithium diisopropylamide , carbanion , chemistry , alkylation , reagent , silylation , acetophenone , ether , organic chemistry , medicinal chemistry , deprotonation , catalysis , ion
Abstract A hydroxy‐directed alkylation of an N , N ‐diethylarylamide using CIPE‐assisted α‐silyl carbanions (CIPE=complex‐induced proximity effect) has been developed using a simple reagent combination of LDA (lithium diisopropylamide) and chlorosilane. A study of the mechanism, and the application of the procedure to an anionic Snieckus–Fries rearrangement for a highly efficient synthesis of the potent phosphatidylinositol 3‐kinase (PI3K) inhibitor LY294002, are reported.