Silyl Ethers as Protective Groups for Alcohols: Oxidative Deprotection and Stability under Alcohol Oxidation Conditions

Abstract

This article reviews the methods which allow the oxidation of either silyl ethers to the corresponding carbonyl compounds or of hydroxy groups in the presence of different silyl ethers. 1. Introduction 2. Chromium Procedures 2.1. Jones Reagent 2.2. Chromium(VI) Oxide-Pyridine Reagents 2.3. Pyridinium Chlorochromate 2.4. Bipyridinium Chlorochromate 2.5. Benzyltrimethylammonium Chlorochromate 2.6. Pyridinium Fluorochromate 2.7. Pyridinium Dichromate and Related Procedures 2.8. Trimethylsilyl Chlorochromate 2.9. Bis(triphenylsilyl) Chromate Catalyzed Oxidation by tert-Butyl Hydroperoxide 3. DMSO Based reagents 4. N-Bromosuccinimide 4.1. Photochemical Procedure 4.2. Thermal Procedure 5. 2,3-Dichloro-5,6-dicyanoquinone 5.1. Thermal Procedure 5.2. Photochemical Procedure 6. Triphenylcarbenium Salts 7. Nitrosonium Tetrafluoroborate 8. Ceric Ammonium Nitrate Catalyzed Oxidation with Sodium Bromate 9. Ruthenium-Induced Oxidations 9.1. Ruthenium Chloride Catalyzed Oxidation by Potassium Persulfate 9.2. Tetrapropylammonium Perruthenate Catalyzed Oxidation by N-Methylmorpholine N-Oxide 9.3. Ruthenium Oxide Catalyzed Oxidation by Sodium Periodate 10. Silver Carbonate on Celite 11. Manganese Procedures 11.1. Manganese Dioxide 11.2. Potassium Permanganate 12. Dess-Martin Periodinane 13. Collective Charts and Concluding Remarks