Addition of electrophilic and heterocyclic carbon-centered radicals to glyoxylic oxime ethers.
[reaction: see text] Stabilized primary radicals can be formed from alkyl halides in an atom transfer process with Et(3)B. 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 alpha-amino acid derivatives.
McNabb
Stephen B
SB
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Ueda
Masafumi
M
Naito
Takeaki
T
D000596:Amino Acids / Q000138:chemical synthesis; D002244:Carbon / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D006038:Glyoxylates / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D010091:Oximes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D004987:Ethers; D005609:Free Radicals; D006038:Glyoxylates; D006571:Heterocyclic Compounds; D010091:Oximes; D002244:Carbon