Synthesis of fused or not β-lactam-biaryl hybrids by free radical aryl-aryl coupling of 2-azetidinone-tethered haloarenes |
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| Authors: | Benito Alcaide,Pedro Almendros,Alberto Rodrí guez-Vicente |
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| Affiliation: | a Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense de Madrid, 28040 Madrid, Spain
b Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain |
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| Abstract: | cis and trans-Aryl-2-azetidinone-tethered haloarenes can be stereoselectively prepared using the ketene-imine cyclization. These β-lactam-tethered haloarenes were used for the regiocontrolled preparation of β-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. |
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| Keywords: | Lactams Nitrogen heterocycles Biaryls Radical reactions Polycycles Cycloaddition |
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