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Citation
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HERO ID
5177483
Reference Type
Journal Article
Title
Diastereoselective access to chiral non-racemic 1,3 oxazolo 2,3-a isoindol-5-one ring systems via O-cationic cyclization
Author(s)
Sikoraiova, J; Chihab-Eddine, A; Marchalin, S; Daich, A
Year
2002
Is Peer Reviewed?
Yes
Journal
Journal of Heterocyclic Chemistry
ISSN:
0022-152X
Publisher
WILEY
Location
HOBOKEN
Volume
39
Issue
2
Page Numbers
383-390
Language
English
DOI
10.1002/jhet.5570390223
Web of Science Id
WOS:000175524200023
URL
http://
://CCC:000175524200023http://www.wiley.com/WileyCDA/
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Abstract
The title compounds 4 have been prepared from suitable beta-amino-alcohol 2 and phthalic anhydride (5) in a three-step sequence in moderate to good yields (58-94%). The key step of this methodology is based on an intramolecular O-cationic cyclization involving N-acyliminium. species. The high levels of the observed chemoselectivity during the intermolecular or intramolecular cyclization were also discussed.
Keywords
Polymer Science; bicyclic lactams, isoindolin-1-one derivatives, pi-cyclizations, facile,; reactivity, nucleophiles, analogs
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