Lewis acid mediated functionalization of β-lactams:: mechanistic study and synthesis of C-3 unsymmetrically disubstituted azetidin-2-ones

被引：15
|
作者：
Bhalla, Arnan [1 ]
Rathee, Suman [1 ]
Madan, Sachin [1 ]
Venugopalan, Paloth [1 ]
Bari, Shamsher S. [1 ]
机构：
[1] Panjab Univ, Dept Chem, Chandigarh 160014, India
来源：
TETRAHEDRON LETTERS | 2006年 / 47卷 / 30期
关键词：
azetidin-2-ones; Lewis acid; nucleophiles; monosubstituted beta-lactams; unsymmetrically disubstituted azetidin-2-ones;
D O I：
10.1016/j.tetlet.2006.05.160
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A convenient and efficient route to novel unsymmetrically disubstituted azetidin-2-ones is described. beta-Lactam carbocation equivalents of type 1 and active aromatic substrates in the presence of a Lewis acid promote a facile and stereoselective C-3 substitution to provide monosubstituted beta-lactams (3,4) and symmetrically disubstituted beta-lactams (5). cis-3-(4'-Methoxyphenyl)3-phenylthioazetidin-2-ones (4) undergo further substitution with active aromatic substrates mediated by a Lewis acid to afford unsymmetrically disubstituted azetidin-2-ones (7). (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5255 / 5259
页数：5
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