Creating carbon-carbon bonds with samarium diiodide for the synthesis of modified amino acids and peptides

In this perspective, an overview of our experiences on the application of samarium diiodide in organic synthesis for the preparation of amino acid and peptide analogues is presented. Three different carbon-carbon bond forming reactions are discussed, including side chain introductions, gamma-amino a...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2006-01, Vol.4 (19), p.3553-3564
Main Authors: Ebran, Jean-Philippe, Jensen, Christina M, Johannesen, Sine A, Karaffa, Jakob, Lindsay, Karl B, Taaning, Rolf, Skrydstrup, Troels
Format: Article
Language:English
Subjects:
Alkylation
Amides - chemical synthesis
Amides - chemistry
Amino Acids - chemical synthesis
Amino Acids - chemistry
Carbon - chemistry
Esters - chemistry
Fumarates - chemical synthesis
Fumarates - chemistry
Glycine - chemistry
Glycosylation
Iodides - chemistry
Ketones - chemistry
Nitrogen - chemistry
Peptides - chemical synthesis
Peptides - chemistry
Samarium - chemistry
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Summary:In this perspective, an overview of our experiences on the application of samarium diiodide in organic synthesis for the preparation of amino acid and peptide analogues is presented. Three different carbon-carbon bond forming reactions are discussed, including side chain introductions, gamma-amino acid synthesis and acyl-like radical additions for the construction of C-C mimics of the peptidic bonds.
ISSN:1477-0520
1477-0539
DOI:10.1039/b608028f