Are stable atropisomers possible for meta-meta' linked biphenols?
| Autor: | John M. Brown, Andrew Mattison, Nathaniel W. Alcock, Duncan Carmichael |
|---|---|
| Přispěvatelé: | University of Oxford [Oxford], Laboratoire de chimie moléculaire (LCM), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-École polytechnique (X), University of Warwick [Coventry] |
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
Atropisomer
010405 organic chemistry Stereochemistry Chemistry [CHIM.ORGA]Chemical Sciences/Organic chemistry Organic Chemistry Diastereomer Atropisomers Circular dichroism 010402 general chemistry 01 natural sciences Biochemistry NMR 0104 chemical sciences X-ray Reduced sugars DFT Computation Axial chirality Drug Discovery [CHIM.CRIS]Chemical Sciences/Cristallography Configurational stability Computational analysis Chirality (chemistry) Linker |
| Zdroj: | Tetrahedron Tetrahedron, Elsevier, 2021, 87, pp.132114. ⟨10.1016/j.tet.2021.132114⟩ |
| ISSN: | 0040-4020 |
| DOI: | 10.1016/j.tet.2021.132114⟩ |
| Popis: | International audience; This paper describes the synthesis, structure, conformation and configurational stability of novel 8-atom meta-meta’ linked biaryls, as models for controlling the ratio of atropisomers through remote central chirality. The synthesis of model compounds is described where the configuration of the linker is provided by reduced C4 and C6 sugars. Their properties have been examined by X-ray, NMR and ECD. Taken together, they provide information on the conformation of the linking chain in each case and indicate a barrier to atropisomerisation in the region of 55 kJ mol−1. For the diastereomeric C6 compounds, the preferred atropisomer is defined by the configuration of the backbone secondary methyl groups. Computational analysis confirms the direction of axial chirality from ECD spectra and offers a model for the distinction between the (R,R,R,R) and (S,R,R,S) C6-isomers.. |
| Databáze: | OpenAIRE |
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