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

Authors
Chihab-Eddine, A Daich, A Jilale, A Decroix, B
Citation
A. Chihab-eddine et al., Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: an application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on pi-cationic cyclization, TETRAHEDR L, 42(4), 2001, pp. 573-576
Citations number
31
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
4
Year of publication
2001
Pages
573 - 576
Database
ISI
SICI code
0040-4039(20010122)42:4<573:SARO(T>2.0.ZU;2-L
Abstract
Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficient ly in four steps from N-alkylated maleimides via, successively, sulfurizati on, regioselective reduction followed by pi -cationic cyclination of the N- acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequence of the dehydration reaction. (C) 2001 Elsevier Sc ience Ltd. All rights reserved.