Synthesis of fused or not β-lactam-biaryl hybrids by free radical aryl-aryl coupling of 2-azetidinone-tethered haloarenes

被引:15
作者
Alcaide, B [1 ]
Almendros, P
Pardo, C
Rodríguez-Vicente, A
Ruiz, MP
机构
[1] Univ Complutense Madrid, Fac Quim, Dept Quim Organ 1, E-28040 Madrid, Spain
[2] CSIC, Inst Quim Organ Gen, E-28006 Madrid, Spain
关键词
lactams; nitrogen heterocycles; biaryls; radical reactions; polycycles; cycloaddition;
D O I
10.1016/j.tet.2005.06.019
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
cis and trans-Aryl-2-azetidinone-tethered haloarenes can be stereoselectively prepared using the ketene-imine cyclization. These beta-lactam-tethered haloarenes were used for the regiocontrolled preparation of beta-lactam-biaryl hybrids including fused tetracyclic biaryl-2-azetidinones as well as C4-dearylated not fused biphenyl-2-azetidinones via aryl-aryl radical cyclization and/or rearrangement. Alternatively, trans-dibenzocarbacephems could be stereoselectively prepared, both in racemic and enantiopure form, through the Staudinger reaction between phenanthridine and activated ketenes. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7894 / 7906
页数:13
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