Stereoselective iodocyclisation of 3-acylamino-2-methylene alkanoates: a computational insight |
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| Authors: | Roberta Galeazzi Gianluca Martelli Giovanna Mobbili Mario Orena Samuele Rinaldi |
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| Institution: | Dipartimento di Scienze dei Materiali e della Terra, Università Politecnica delle Marche, Via Brecce Bianche, I-60131 Ancona, Italy |
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| Abstract: | In order to explain the high stereocontrol occurring in the iodocyclisation of 3-acylamino-2-methylenealkanoates, either the conformational space of the starting products or the cyclisation reaction potential energy surface (PES) was explored at DFT level of theory, the polarised continuum formalism (PCM) for chloroform being used in order to consider the solvent effect. The observed stereoselection was ascribed to both the near attack conformations (NACs) distribution and the energy differences between the two possible and competitive cyclisation pathways leading to cis- and trans-diastereomers. |
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