DOI QR코드

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Stereospecific C$_6$-Hydroxyethylation of the Penicillin Nucleus

  • Kim, Wan-Joo (Division of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Lee, Gwan-Sun (Division of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Shim, Sang-Chul (Division of Chemistry, Korea Advanced Institute of Science and Technology)
  • 발행 : 1984.10.20

초록

6, 6-Diiodopenicillanic acid was prepared from 6-aminopenicillanic acid using iodine-sodium iodide systems in good yield (60%). Enolates derived from 6-chloro-6-iodo-, 6,6-diiodo-penicillanate have been generated in situ by a metal-halogen exchange process at -$78^{\circ}C$ using methylmangnesium iodide and reacted with acetaldehyde to yield aldols. As the size of remaining halogen atom increases, the proportion of ${\beta}$-face attack was increased. In the case of 6,6-diiodopenicillanate, only ${\beta}$-face attack was observed yielding a single isomer (6S, 8R).

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참고문헌

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피인용 문헌

  1. ChemInform Abstract: STEREOSPECIFIC C-6 HYDROXYETHYLATION OF THE PENICILLIN NUCLEUS vol.16, pp.23, 1985, https://doi.org/10.1002/chin.198523362