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Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids
Masafumi Ueda,Hideto Miyabe,Hisako Sugino,Takeaki Naito
Organic & Biomolecular Chemistry Pub Date : 02/21/2005 00:00:00 , DOI:10.1039/B418726A
Abstract

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 α-amino acids. The diastereoselectivities observed in the reaction of hydrazones were better than those obtained in the reaction of oxime ethers.

Graphical abstract: Zinc-mediated carbon radical addition to glyoxylic imines in aqueous media for the synthesis of α-amino acids
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