Computational Studies on the Synthesis of β-Lactams via [2+2] Thermal Cycloadditions
作者： Ana Arrieta , Begoña Lecea , Fernando P. Cossío
DOI: 10.1007/7081_2009_10
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摘要: The main computational studies on the formation of β-lactams through [2+2] cycloadditions published during 1992–2008 are reported with special emphasis mechanistic and selectivity aspects these reactions. Disconnection N1-C2 C3–C4 bonds azetidin-2-one ring leads to reaction between ketenes imines. Computational experimental results point a stepwise mechanism for this reaction. first step consists nucleophilic attack iminic nitrogen sp-hybridized carbon atom ketene. zwitterionic intermediate thus formed yields corresponding β-lactam by means four-electron conrotatoty electrocyclization. steroecontrol periselectivity support two-step mechanism. cycloaddition isocyanates alkenes takes place via concerted (but asynchronous) that can be interpreted in terms [π2s + (π2s π2s)] interaction both reactants. Both regio stereochemistry observed compatible model. However, combination solvent substituent effects result
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