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
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Chemistry
Exact sciences and technology
Organic chemistry
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container_end_page 10301
container_issue 35
container_start_page 10300
container_title Journal of the American Chemical Society
container_volume 124
creator Aggarwal, Varinder K
Sheldon, Chris G
Macdonald, Gregor J
Martin, William P
description 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.
doi_str_mv 10.1021/ja027061c
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Exact sciences and technology
Organic chemistry
title A New Method for the Preparation of Silyl Enol Ethers from Carbonyl Compounds and (Trimethylsilyl)diazomethane in a Regiospecific and Highly Stereoselective Manner
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