Novel binaphthyl and biphenyl α- and β-amino acids and esters: Organocatalysis of asymmetric Diels-Alder reactions. A combined synthetic and computational study

Bulman Page, Philip C., Kinsey, Francesca S., Chan, Yohan, Strutt, Ian R., Slawin, Alexandra M.Z. and Jones, Garth A. (2018) Novel binaphthyl and biphenyl α- and β-amino acids and esters: Organocatalysis of asymmetric Diels-Alder reactions. A combined synthetic and computational study. Organic and Biomolecular Chemistry, 16 (40). pp. 7400-7416. ISSN 1477-0520

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Abstract

Asymmetric catalysis of the Diels-Alder reaction between cyclopentadiene and cinnamaldehydes has been studied using as catalysts a range of novel α- and β-aminoacids and aminoesters with binaphthyl and biphenyl backbones, providing enantioselectivities of up to 62% ee. B3LYP/6-31G* calculations, including free energy corrections, have been carried out on a binaphthyl catalyst example to identify transition state structures and to aid in the identification of major enantiomers. The calculated product ratios agree well with the experimental data; the transition states identified involve preferential approach of cyclopentene along a trajectory adjacent to the acid/ester group. The four lowest energy transition states display a stabilizing dipolar interaction between the carbonyl group oxygen atom and a terminal proton of the diene unit.

Item Type: Article
Additional Information: Funding Information: This investigation has enjoyed the support of EU Interreg IVA (project 4061) and the University of East Anglia. We are also indebted to the EPSRC National Mass Spectrometry Facility at Swansea University.
Uncontrolled Keywords: biochemistry,physical and theoretical chemistry,organic chemistry,sdg 7 - affordable and clean energy ,/dk/atira/pure/subjectarea/asjc/1300/1303
Faculty \ School: Faculty of Science > School of Chemistry
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Depositing User: LivePure Connector
Date Deposited: 02 Feb 2022 15:30
Last Modified: 23 Oct 2022 03:30
URI: https://ueaeprints.uea.ac.uk/id/eprint/83270
DOI: 10.1039/c8ob01795f

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