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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 20, Number 3
BKCSDE 20(3)
March 20, 1999 

Deastereoselectivity in the Reaction of 2-Piperidineacetates
Hyun-Kyu Chung, Hyung-Woo Kim, Kyoo-Hyun Chung
In the reactions of the enolates of various 2-piperidineacetates with iodomethane or trisyl azide, the anti isomer was always predominant over the syn one, independent of the stereochemistry of the piperidineacetates. The piperidineacetates having OTBDMS moiety at C5 proceeded more diastereoselectively than the compounds without the substituent. The diastereoselectivity could be explained by perpendicular model for the electrophilic substitution reaction.
325 - 328
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