Absolute Configuration Assignment of a Paraconic Acid Derivative via Vibrational Circular Dichroism Spectroscopy and Density Functional Theory Calculation |
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Authors: | Sara Meninno Paola Rizzo Sergio Abbate Giovanna Longhi Giuseppe Mazzeo Guglielmo Monaco Alessandra Lattanzi Riccardo Zanasi |
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Institution: | 1. Dipartimento di Chimica e Biologia “Adolfo Zambelli”, Università degli Studi Salerno, Fisciano, (SA), Italy;2. Dipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Brescia, Italy |
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Abstract: | Density functional theory calculation of the vibrational circular dichroism spectrum was used to assign the absolute configuration of an all‐carbon quaternary β‐stereocenter of a γ‐butyrolactone recently synthesized through an asymmetric organocatalytic tandem aldol/lactonization sequence. Comparison with the experimental spectrum is satisfactory, on account of the fact that spectroscopic features are weak due to the presence of multiple conformers. As a result, the (R) absolute configuration was assigned to the (+) optical isomer. Chirality 28:110–115, 2016. © 2015 Wiley Periodicals, Inc. |
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Keywords: | absolute configuration density functional theory vibrational circular dichroism γ ‐butyrolactones quaternary stereocenters paraconic acid derivatives |
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