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
Identifieur interne : 001761 ( Main/Exploration ); précédent : 001760; suivant : 001762Synthesis 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
Auteurs : Abderrahim Chihab-Eddine [Maroc] ; Adam Da Ch [France] ; Abderrahim Jilale [Maroc] ; Bernard Decroix [France]Source :
- Tetrahedron Letters [ 0040-4039 ] ; 2001.
English descriptors
Abstract
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.
Url:
DOI: 10.1016/S0040-4039(00)02037-2
Affiliations:
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Le document en format XML
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<front><div type="abstract" xml:lang="en">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.</div>
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