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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 5, Number 5
BKCSDE 5(5)
May 20, 1984 

 
Title
Stereospecific C6-Hydroxyethylation of the Penicillin Nucleus
Author
Wan Joo Kim, Gwan Sun Lee, Sang Chul Shim
Keywords
Abstract
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℃ using methylmangnesium iodide and reacted with acetaldehyde to yield aldols. As the size of remaining halogen atom increases, the proportion of β-face attack was increased. In the case of 6,6-diiodopenicillanate, only β-face attack was observed yielding a single isomer (6S, 8R).
Page
191 - 193
Full Text
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