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

被引：30
作者：
Chihab-Eddine, A
Daïch, A
Jilale, A
Decroix, B
机构：
[1] Univ Havre, Fac Sci & Tech, URCOM, Chim Lab, F-76058 Le Havre, France
[2] Univ Ibnou Zohr, Fac Sci, Dept Chim, Lab Bioorgan, Agadir, Morocco
来源：
TETRAHEDRON LETTERS | 2001年 / 42卷 / 04期
关键词：
N-acyliminium ion; pi-cationic cyclization; aza-compounds; isothiochroman; benzo[d]thiepine;
D O I：
10.1016/S0040-4039(00)02037-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, 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 Science Ltd. All rights reserved.
引用
收藏
页码：573 / 576
页数：4
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