Addition of Electrophilic and Heterocyclic Carbon-Centered Radicals to Glyoxylic Oxime Ethers

Stabilized primary radicals can be formed from alkyl halides in an atom transfer process with Et3B. This process depends on the strength of the carbon−halogen bond and the stability of the resulting primary radical. Radicals formed from benzyl iodide and ethyl iodoacetate add to glyoxylic oxime ethe...

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Bibliographic Details
Published in:Organic letters 2004-06, Vol.6 (12), p.1911-1914
Main Authors: McNabb, Stephen B, Ueda, Masafumi, Naito, Takeaki
Format: Article
Language:English
Subjects:
Amino Acids - chemical synthesis
Carbon - chemistry
Ethers - chemical synthesis
Ethers - chemistry
Free Radicals - chemistry
Glyoxylates - chemical synthesis
Glyoxylates - chemistry
Heterocyclic Compounds - chemistry
Molecular Conformation
Oximes - chemical synthesis
Oximes - chemistry
Stereoisomerism
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Summary:Stabilized primary radicals can be formed from alkyl halides in an atom transfer process with Et3B. This process depends on the strength of the carbon−halogen bond and the stability of the resulting primary radical. Radicals formed from benzyl iodide and ethyl iodoacetate add to glyoxylic oxime ethers; however, more electrophilic radicals do not. Glyoxylic oxime ethers are also good radical acceptors for heterocyclic carbon-centered secondary radicals, giving novel α-amino acid derivatives.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol049671i