Application of Silicon-based Methodologies for the Synthesis of Functionalized Mono- and Bisphosphonic Acids

Author(s): Vadim D. Romanenko, Michael V. Shevchuk, Valery P. Kukhar

Journal Name: Current Organic Chemistry

Volume 15 , Issue 16 , 2011


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Abstract:

The aim of this article is to present an overview of new and useful silicon-based methodologies valuable for the selective construction of highly functionalized mono- and bisphosphonic acids of high synthetic and biological importance. The reactions of trimethylsilyl phosphites with alkyl halides, carbonyl compounds and imines are presented as a platform for developing new approaches to biologically active hydroxy-, amino-, fluoro-substituted mono- and bisphosphonates. The second part of the review consists of a presentation of methodology involving the fluoride-induced formation of α-phosphonylated carbanions from 1-trimethylsilyl methylphosphonates. The third part of the review describes the methodology employing silylated phosphonate carbanions. Application of trimethylsilyl as protecting group is discussed in separate section.

Keywords: Silicon, phosphonic acids, bisphosphonic acids, organosilicon-mediated synthesis, phosphites, herbicides, pesticides, antibiotics, antiviral, antitumor agents, enzyme inhibitors, calcium metabolism, osteolysis, hexamethyldisilazane (HMDS), phosphocarnitine

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Article Details

VOLUME: 15
ISSUE: 16
Year: 2011
Page: [2774 - 2801]
Pages: 28
DOI: 10.2174/138527211796378505
Price: $58

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