Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of alpha-amino acids.
The addition of carbon radicals to glyoxylic imines was studied using zinc dust as a radical initiator. The zinc-mediated radical reaction of glyoxylic oxime ethers and hydrazones proceeded smoothly to give the alkylated products via a carbon-carbon bond-forming process in aqueous media. The reaction of the oxime ethers and hydrazones having an Oppolzer's camphorsultam group provided the corresponding alkylated products, which could be converted into enantiomerically pure alpha-amino acids. The diastereoselectivities observed in the reaction of hydrazones were better than those obtained in the reaction of oxime ethers.
Ueda
Masafumi
M
Kobe Pharmaceutical University, Motoyamakita, Higashinada, Kobe 658-8558, Japan.
Miyabe
Hideto
H
Sugino
Hisako
H
Naito
Takeaki
T
D000596:Amino Acids / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry*; D006038:Glyoxylates / Q000737:chemistry*; D006835:Hydrazones / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015032:Zinc / Q000494:pharmacology*
D000596:Amino Acids; D004987:Ethers; D005609:Free Radicals; D006038:Glyoxylates; D006835:Hydrazones; D007097:Imines; C482355:glyoxylic oxime ether; D002244:Carbon; D015032:Zinc