Carbon–carbon bond construction on solid support: triethylborane-induced radical reactions of oxime ethers

The triethylborane-induced solid-phase radical reaction was studied. The solid-phase radical reaction of oxime ether anchored to Wang resin proceeded smoothly to give the α-amino acid derivatives. The carbon–carbon bond-forming radical reaction of TentaGel OH resin-bound glyoxylic oxime ether procee...

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Bibliographic Details
Published inTetrahedron Vol. 59; no. 11; pp. 1901 - 1907
Main Authors Miyabe, Hideto, Nishimura, Azusa, Fujishima, Yumi, Naito, Takeaki
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 10.03.2003
Elsevier
Subjects
amino acids
Chemistry
Chemistry, Organic
oxime ethers
Physical Sciences
radical reactions
Science & Technology
solid-phase reactions
radical reactions
oxime ethers
amino acids
solid-phase reactions
PHASE ORGANIC-REACTIONS
ASYMMETRIC-SYNTHESIS
ALPHA-AMINO-ACIDS
GAMMA-BUTYROLACTONES
DIETHYLZINC
ADDITION-CYCLIZATION REACTION
CHEMISTRY
DERIVATIVES
WATER
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Summary:The triethylborane-induced solid-phase radical reaction was studied. The solid-phase radical reaction of oxime ether anchored to Wang resin proceeded smoothly to give the α-amino acid derivatives. The carbon–carbon bond-forming radical reaction of TentaGel OH resin-bound glyoxylic oxime ether proceeded even in aqueous media. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(03)00154-6