Synthesis and reactivity of (1 S)- N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[ d]thiepine based on π-cationic cyclization

Chiral pyrroloisothiochroman and pyrrolo[ d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate e...

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Bibliographic Details
Published in:Tetrahedron letters 2001-01, Vol.42 (4), p.573-576
Main Authors: Chihab-Eddine, Abderrahim, Daı̈ch, Adam, Jilale, Abderrahim, Decroix, Bernard
Format: Article
Language:English
Subjects:
aza-compounds
benzo[ d]thiepine
isothiochroman
N-acyliminium ion
π-cationic cyclization
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Summary:Chiral pyrroloisothiochroman and pyrrolo[ d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(00)02037-2