Reagents for Carbonyl Methylenation in Organic Synthesis

Ian      Beadham; Jason      Micklefield

doi:10.2174/1570179053545396

Abstract

The methylenation of carbonyl compounds in the areas of natural and non-natural products chemistry is described herein. Phosphorus, sulfur and silicon-based reagents are compared with more recent systems based on boron, zinc and titanium and the relative merits of each reagent are discussed. Particular attention is paid to methods, which can overcome the problems associated with sterically hindered or enolizable aldehydes and ketones.

Keywords: olefination, methylenation, carbonyl compounds, enolizable ketones, hindered ketones

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Current Organic Synthesis

Title: Reagents for Carbonyl Methylenation in Organic Synthesis

Volume: 2 Issue: 2

Author(s): Ian Beadham and Jason Micklefield

Affiliation:

Keywords: olefination, methylenation, carbonyl compounds, enolizable ketones, hindered ketones

Abstract: The methylenation of carbonyl compounds in the areas of natural and non-natural products chemistry is described herein. Phosphorus, sulfur and silicon-based reagents are compared with more recent systems based on boron, zinc and titanium and the relative merits of each reagent are discussed. Particular attention is paid to methods, which can overcome the problems associated with sterically hindered or enolizable aldehydes and ketones.

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Beadham Ian and Micklefield Jason, Reagents for Carbonyl Methylenation in Organic Synthesis, Current Organic Synthesis 2005; 2 (2) . https://dx.doi.org/10.2174/1570179053545396