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Kinetic Resolution in the [2+2] Cycloaddition of Ketenes: An Experimental and Theoretical Study |
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| Authors: | Pauline Rullière Dr Sébastien Carret Prof Anne Milet Prof Jean‐François Poisson |
| Institution: | 1. Université Joseph Fourier, CNRS, Département de Chimie Moléculaire, SERCO, UMR 5250, ICMG FR‐2607, BP 53, 38041 Grenoble CEDEX 9 (France), Fax: (+33)?4‐76‐63‐57‐54;2. Département de Chimie Moléculaire, équipe Chimie Théorique, UMR 5250, ICMG FR‐2607, CNRS, Université Joseph Fourier, BP 53, 38041 Grenoble CEDEX 9 (France), Fax: (+33)?4‐76‐63‐57‐54 |
| Abstract: | The kinetic resolution of Z and E olefins by 2+2] cycloaddition with ketenes allows the isolation of pure E olefin, as well as the synthesis of pure cis‐cyclobutanones, starting from Z/E mixtures. A computational rationale for this kinetic difference is reported. The obtained difference of energy of activation matches with the experimental results. |
| Keywords: | cycloaddition ketenes kinetic resolution olefins stereochemistry |