Download PDF
Synthesis 1977; 1977(2): 91-110
DOI: 10.1055/s-1977-24284
review
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

O-Silylated Enolates - Versatile Intermediates for Organic Synthesis

Jerald K. RASMUSSEN*
  • *Central Research Laboratories, 3M Company, P. O. Box 33221, St. Paul, Minnesota 55133, U. S. A.
Further Information

Publication History

Publication Date:
12 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Recent developments in the preparation and reactions of silyl enol ethers derived from aldehydes, ketones, and carboxylic acids and esters are discussed. These versatile compounds provide tremendous potential as synthetic enol equivalents. 1. Synthesis of Silyl Enol Ethers 1.1. Preparation from Enolates 1.2. Preparation from Hydrosilanes 1.3. Preparation from Other Silylating Agents 1.4. Preparation by Thermal Rearrangements 2. Synthesis of Ketene Silyl Acetals 2.1. Preparation from α-Anions and Dianions 2.2. Preparation by Hydrosilylation 3. Reactions of Silylated Enols 3.1. Preparation of Directed Enolates 3.2. Addition of Halides to the Double Bond 3.3. Reactions with Hydrogen Halides 3.4. Cycloaddition Reactions 3.5. Oxidation of Silyl Enol Ethers 3.6. Titanium(IV) Chloride Promoted Reactions 3.7. Thermal Rearrangements of Ketene Silyl Acetals 4. Conclusion