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Molecules 2016, 21(12), 1704; doi:10.3390/molecules21121704

Sugar-Annulated Oxazoline Ligands: A Novel Pd(II) Complex and Its Application in Allylic Substitution

Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Author to whom correspondence should be addressed.
Academic Editor: Rafael Chinchilla
Received: 25 October 2016 / Revised: 1 December 2016 / Accepted: 7 December 2016 / Published: 10 December 2016
(This article belongs to the Special Issue Asymmetric Synthesis 2017)
View Full-Text   |   Download PDF [3503 KB, uploaded 10 December 2016]   |  


Two novel carbohydrate-derived pyridyl (PYOX)- and cyclopropyl (CYBOX)-substituted oxazoline ligands were prepared from d-glucosamine hydrochloride and 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-d-glucopyranose hydrochloride in two steps, respectively. The sugar-annulated PYOX ligand formed a stable metal complex with Pd(II), which was fully characterized by NMR spectroscopy and X-ray crystallography. NMR and X-ray analysis revealed a change of the conformation in the sugar moiety upon complexation with the palladium(II) species. Both glycosylated ligands resulted in high asymmetric induction (up to 98% ee) upon application as chiral ligands in the Pd-catalyzed allylic alkylation of rac-1,3-diphenylallyl acetate with dimethyl malonate (Tsuji-Trost reaction). Both ligands provided mainly the (R)-enantiomer of the alkylation product. View Full-Text
Keywords: asymmetric catalysis; carbohydrates; oxazolines; palladium complexes; pyridines; Tsuji-Trost asymmetric catalysis; carbohydrates; oxazolines; palladium complexes; pyridines; Tsuji-Trost

This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Kraft, J.; Mill, K.; Ziegler, T. Sugar-Annulated Oxazoline Ligands: A Novel Pd(II) Complex and Its Application in Allylic Substitution. Molecules 2016, 21, 1704.

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