Advances in Organic Synthesis

Volume: 2

Modern Organofluorine Chemistry-Synthetic Aspects

Indexed in: Chemical Abstracts, EBSCO, Ulrich's Periodicals Directory

The volume focuses on recent advances in organofluorine chemistry directed towards selective fluorine introduction into various target molecules, employing both traditional and contemporary, ...
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Synthetic Utility of Fluorinated β-Keto-Phosphonium Salts, - Phosphonates and Related Compounds

Pp. 523-572 (50)

Yanchang Shen

Abstract

Sequential transformations have attracted much interest in recent years because they provide simple and efficient entry into complex compounds by including two or more steps in a single operation to increase the complexity of the substrate, starting from commercially available, relatively simple precursors. The new methodologies discussed in this review chapter are based on sequential transformations and possess high stereoselectivity. They include the synthetic utility of fluorinated β-keto-phosphonium salts, “one-pot” carbon-carbon double bond formation, ylide-ion formation resulting from nucleophilic addition, stereocontrolled olefination method, alkenylation based on elimination of triphenylarsine, reductive olefination mediated by Ti(O-i-Pr)4 and Ph3P and sequential transformation of organophosphorus compounds in organic synthesis. The newly discussed methodologies are, therefore, potentially useful in organic synthesis particularly in the medicinal and agricultural chemistry for the synthesis of biologically active compounds.

Affiliation:

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.