Ortho-Silylated Derivatives of Tetrakis(2-hydroxyphenyl)ethene: A Sterically Isolated Structural Model for Oxo-Surface Binding Domains

The introduction of sterically isolating ortho-trialkylsilyl, -aryldialkylsilyl, and -diarylalkylsilyl substituents onto the structurally preorganized tetrakis(2-hydroxyphenyl)ethene ligand framework has been accomplished by a 4-fold retro-Brook rearrangement. Installation of the most sterically dem...

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Bibliographic Details
Published in:Organic letters 2008-09, Vol.10 (17), p.3825-3828
Main Authors: Chung, Mee-Kyung, Lightbody, Owen C, Stryker, Jeffrey M
Format: Article
Language:English
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Summary:The introduction of sterically isolating ortho-trialkylsilyl, -aryldialkylsilyl, and -diarylalkylsilyl substituents onto the structurally preorganized tetrakis(2-hydroxyphenyl)ethene ligand framework has been accomplished by a 4-fold retro-Brook rearrangement. Installation of the most sterically demanding silyl substituents required the development of an iterative procedure, involving successive double silylation/metalation/migration sequences without the isolation of intermediates. This system was designed to function as a soluble structural model for the planar binding domains of heterogeneous “oxo-surfaces” of silica and alumina supports.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol801427w