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Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls. | LitMetric

AI Article Synopsis

  • The research describes a chemical process where a zinc-organometallic compound is created using a specific reaction involving a beta-keto carbonyl.
  • By exposing this intermediate to trimethylsilyl chloride and iodine, a product known as alpha-iodomethyl-gamma-keto carbonyl is specifically formed.
  • This new iodomethyl group can be further modified to develop side chains that resemble those found in alpha-amino acids, which could have implications in various chemical or biological applications.

Article Abstract

Sequential exposure of a zinc-organometallic intermediate, generated through a zinc carbenoid-mediated chain extension reaction of a beta-keto carbonyl, to trimethylsilylchloride and iodine provided regioselective formation of an alpha-iodomethyl-gamma-keto carbonyl. The iodomethyl functionality can be further manipulated to provide side chains that are potential mimics of alpha-amino acid side chains.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2598404PMC
http://dx.doi.org/10.1016/j.tet.2008.06.063DOI Listing

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