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

页码：573 / 576

页数：4

共 2 条

[1] Studies on (1S)-N-(1-phenylethyl)phthalimide:: Synthesis of both chiral spiro indane and benzazepine derivatives
Chihab-Eddine, A
Daïch, A
Jilale, A
Decroix, B
HETEROCYCLES, 2002, 58 : 449 - 456
[2] Bischler-Napieralski cyclization of N-[2-(2-bromo-5-hydroxy-4-methoxyphenyl)ethyl]-N-[(S)-1-phenylethyl]-2-(2-bromo-4,5-dimethoxyphenyl)acetamide accompanied by elimination of chiral auxiliary
Miyatani, K
Ohno, M
Tatsumi, K
Ohishi, Y
Kunitomo, J
Kawasaki, I
Yamashita, M
Ohta, S
HETEROCYCLES, 2001, 55 (03) : 589 - 595

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