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

Dedicated to Professor Jean Morel for his retirement The title compounds 4 have been prepared from suitable β‐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 cycliza...

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Veröffentlicht in:Journal of heterocyclic chemistry 2002-03, Vol.39 (2), p.383-390
Hauptverfasser: Sikoraiová, Jana, Marchalín, ŠTefan, Chihab‐Eddine, Abderrahim, Daïch, Adam
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Sprache:eng
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Zusammenfassung:Dedicated to Professor Jean Morel for his retirement The title compounds 4 have been prepared from suitable β‐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