Journal
ISRAEL JOURNAL OF CHEMISTRY
Volume 52, Issue 1-2, Pages 76-91Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ijch.201100082
Keywords
[2; 2]paracyclophane; Friedel-Crafts alkylation; Hantzsch's ester; hydrogen bonds; organocatalysis; planar-chiral; thiourea; transfer hydrogenation
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Funding
- Fonds der Chemischen Industrie
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The development of planar-chiral hydrogen-bond donors based on the [2.2]paracyclophane scaffold is discussed. General strategies to access functionalized enantiopure [2.2]paracyclophane derivatives are briefly reviewed, with the focus on suitable precursors for the synthesis of planar-chiral thiourea derivatives. The synthesis of fourteen hydrogen-bond donors is described. The interaction of four thiourea derivatives with hydrogen-bond acceptors (DMSO and tetramethylammonium chloride) was investigated by 1H NMR spectroscopy and X-ray crystallography. A selection of enantiomerically pure planar-chiral derivatives was applied in asymmetric hydrogen-bond catalysis.
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