Studies on (1S)-N-(1-phenylethyl)phthalimide: Synthesis of both chiral spiro indane and benzazepine derivatives

Chiral spiro indane and benzazepine compounds in isoindolinone series were prepared easily by pi-cationic cyclization of the N-acyliminium ions (5-9) or the acylium ion (17) precursors with trifluoroacetic acid or aluminum trichloride, respectively. The stereochemistry and the ratio of diastereomeri...

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Bibliographic Details
Published inHeterocycles Vol. 58; pp. 449 - 456
Main Authors Chihab-Eddine, A, Daich, A, Jilale, A, Decroix, B
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 22.11.2002
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
Grignard reaction
N-ACYLIMINIUM IONS
CATIONIC CYCLIZATION
N-acyliminium ion
PI-CYCLIZATIONS
REACTIVITY
LACTAMS
diastereoselectivity
INTRAMOLECULAR AMIDOALKYLATION
cyclization
Felkin-Ahn model
ATOM
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Summary:Chiral spiro indane and benzazepine compounds in isoindolinone series were prepared easily by pi-cationic cyclization of the N-acyliminium ions (5-9) or the acylium ion (17) precursors with trifluoroacetic acid or aluminum trichloride, respectively. The stereochemistry and the ratio of diastereomeric mixtures observed during these process were also discussed.
ISSN:0385-5414
1881-0942