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Synthesis 1983; 1983(1): 1-28
DOI: 10.1055/s-1983-30204
review
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Silyl Enol Ethers in Synthesis - Part I

Peter Brownbridge*
  • *University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, England
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Publication Date:
17 May 2002 (online)

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The last few years have seen an explosive growth in the use of silyl enol ethers and silyl ketene acetals in organic synthesis. The aim of this review is to provide a reasonably comprehensive account of the newer reactions of these compounds, illustrated by some examples from synthetic pathways. 1. Introduction 2. Preparation 2.1. Silyl Enol Ethers from Ketones and Aldehydes 2.2. Silyl Enol Ethers from Enones 2.3. Silyl Enol Ethers from Acylsilanes 2.4. Silyl Enol Ethers by Other Methods 2.5. 1-(Trimethylsilyl)-silyl Enol Ethers 2.6. Silyl Ketene Acetals and Related Compounds 3. Reactions 3.1. Protonolysis 3.2. Reduction 3.3. Oxidation 3.4. Reactions with Non-Carbon Electrophiles 3.5. Reactions with Carbon Electrophiles 3.6. Reactions with Carbon Nucleophiles 3.7. Concerted Reactions 4. Siloxybutadienes (Silyl Dienol Ethers) 4.1. Preparation 4.2. Reactions with Electrophiles 4.3. [4+2]-Cycloadditions 5. Addendum 6. Conclusions

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