Diastereoselectivity in the reaction of 2-piperidineacetates

Authors
Chung, HK Kim, HW Chung, KH
Citation
Hk. Chung et al., Diastereoselectivity in the reaction of 2-piperidineacetates, B KOR CHEM, 20(3), 1999, pp. 325-328
Citations number
30
Categorie Soggetti
Chemistry
Journal title
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
ISSN journal
02532964 → ACNP
Volume
20
Issue
3
Year of publication
1999
Pages
325 - 328
Database
ISI
SICI code
0253-2964(19990320)20:3<325:DITRO2>2.0.ZU;2-#
Abstract
In the reactions of the enolates of various 2-piperidineacetates with iodom ethane or trisyl azide, the anti isomer was always predominant over the syn one, independent of the stereochemistry of the piperidineacetates. The pip eridineacetates having OTBDMS moiety at C-5 proceeded more diastereoselecti vely than the compounds without the substituent. The diastereoselectivity c ould be explained by perpendicular model for the electrophilic substitution reaction.