A New Method for the Preparation of Silyl Enol Ethers from Carbonyl Compounds and (Trimethylsilyl)diazomethane in a Regiospecific and Highly Stereoselective Manner

A New Method for the Preparation of Silyl Enol Ethers from Carbonyl Compounds and (Trimethylsilyl)diazomethane in a Regiospecific and Highly Stereoselective Manner

The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI)...

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Veröffentlicht in:Journal of the American Chemical Society 2002-09, Vol.124 (35), p.10300-10301
Hauptverfasser: Aggarwal, Varinder K, Sheldon, Chris G, Macdonald, Gregor J, Martin, William P
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Organic chemistry
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Zusammenfassung:The reaction of lithium (trimethylsilyl)diazomethane with aldehydes and ketones has been investigated, and it has been found that quenching at low temperature with MeOH followed by addition of Rh2(OAc)4 gave silyl enol ethers in high yields. Quenching with other electrophiles (e.g., deuterium, MeI) gave terminal and substituted silyl enol ethers with complete control over regio- and stereochemistry. The mechanism of this novel process has been mapped out through a combination of deuterium labeling, ReactIR, and isolation of reaction intermediates.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja027061c