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

页码：5255 / 5259

页数：5

共 24 条

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