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Origin of the Relative Stereoselectivity of the β-Lactam Formation in the Staudinger Reaction

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    Origin of the Relative Stereoselectivity of the β-Lactam Formation in the Staudinger Reaction
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    Contribution from the Key Laboratory of Biooganic Chemistry and Molecular Engineering of Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2006, 128, 18, 6060–6069
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    https://doi.org/10.1021/ja056711k
    Published April 14, 2006
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    Abstract

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    The relative (cis, trans) stereoselectivity of the β-lactam formation is one of the critical issues in the Staudinger reaction. Although many attempts have been made to explain and to predict the stereochemical outcomes, the origin of the stereoselectivity remains obscure. We are proposing a model that explains the relative stereoselectivity based on a kinetic analysis of the cis/trans ratios of reaction products. The results were derived from detailed Hammett analyses. Cyclic imines were employed to investigate the electronic effect of the ketene substituents, and it was found that the stereoselectivity could not be simply attributed to the torquoelectronic model. Based on our results, the origin of the relative stereoselectivity can be described as follows:  (1) the stereoselectivity is generated as a result of the competition between the direct ring closure and the isomerization of the imine moiety in the zwitterionic intermediate; (2) the ring closure step is most likely an intramolecular nucleophilic addition of the enolate to the imine moiety, which is obviously affected by the electronic effect of the ketene and imine substituents; (3) electron-donating ketene substituents and electron-withdrawing imine substituents accelerate the direct ring closure, leading to a preference for cis-β-lactam formation, while electron-withdrawing ketene substituents and electron-donating imine substituents slow the direct ring closure, leading to a preference for trans-β-lactam formation; and (4) the electronic effect of the substituents on the isomerization is a minor factor in influencing the stereoselectivity.

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    Additional experiments and discussion, detailed kinetic treatment, experimental details, representative spectra for determining the cis/trans ratios, and spectroscopic data and 1H NMR spectra of all β-lactam products. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2006, 128, 18, 6060–6069
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