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Issue 20, 2014
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The nature of persistent conformational chirality, racemization mechanisms, and predictions in diarylether heptanoid cyclophane natural products

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Abstract

Restricted rotations of chemical bonds can lead to the presence of persistent conformational chirality in molecules lacking stereocenters. We report the development of first-of-a-kind predictive rules that enable identification of conformational chirality and prediction of racemization barriers in the diarylether heptanoid (DAEH) natural products that do not possess stereocenters. These empirical rules-of-thumb are based on quantum mechanical computations (SCS-MP2/∞//B3LYP/6-31G*/PCM) of racemization barriers of four representative DAEHs. Specifically, the local symmetry of ring B and the E/Z configuration of the vinylogous acid/ester are critical in determining conformational chirality in the DAEH natural product family.

Graphical abstract: The nature of persistent conformational chirality, racemization mechanisms, and predictions in diarylether heptanoid cyclophane natural products

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Publication details

The article was received on 21 Dec 2013, accepted on 04 Apr 2014 and first published on 04 Apr 2014


Article type: Paper
DOI: 10.1039/C3OB42550A
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 3303-3309
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    The nature of persistent conformational chirality, racemization mechanisms, and predictions in diarylether heptanoid cyclophane natural products

    O. Pattawong, M. Q. Salih, N. T. Rosson, C. M. Beaudry and P. H. Cheong, Org. Biomol. Chem., 2014, 12, 3303
    DOI: 10.1039/C3OB42550A

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