Diastereoselective access to chiral non-racemic [1,3]oxazolo[2,3-a]isoindol-5-one ring systems via O-cationic cyclization

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...

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Bibliographic Details
Published inJournal of heterocyclic chemistry Vol. 39; no. 2; pp. 383 - 390
Main Authors Sikoraiova, J, Chihab-Eddine, A, Marchalin, S, Daich, A
Format Journal Article
LanguageEnglish
Published HOBOKEN Wiley 01.03.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
REACTIVITY
FACILE
BICYCLIC LACTAMS
DERIVATIVES
PI-CYCLIZATIONS
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Summary: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.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.5570390223