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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
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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]   |  

Abstract

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
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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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