Lithiation of a Silyl Ether: Formation of an  ortho ‐Fries Hydroxyketone | Zendy

Lo HongJay | Zendy; Lin ChinYin | Zendy; Tseng MeiChun | Zendy; Chein RongJie | Zendy

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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

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.

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