✦ LIBER ✦
Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization
✍ Scribed by Abderrahim Chihab-Eddine; Adam Daı̈ch; Abderrahim Jilale; Bernard Decroix
- Book ID
- 104211581
- Publisher
- Elsevier Science
- Year
- 2001
- Tongue
- French
- Weight
- 94 KB
- Volume
- 42
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Chiral pyrroloisothiochroman and pyrrolo[d]
thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by p-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction.