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Synfacts 2005(1): 0168-0168  
DOI: 10.1055/s-2005-872221
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

The First Solid-Phase Synthesis of Bis(oxazolinyl)pyridine Ligands

Contributor(s): Yasuhiro Uozumi, Tomohiko Beppu
A. Weisberg, B. Halak, M. Portnoy*
Tel-Aviv University, Israel
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Publikationsdatum:
21. September 2005 (online)

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Significance

The solid-phase synthesis of bis(oxazolinyl)pyridine ligand (Pybox) on Wang resin was described. The pybox ligands (1a-g) were prepared in 66-90% yield. Tertiary Bu-Pybox 1f showed high enantioselectivity for copper-catalyzed asymmetric alkylation of benzylideneaniline with phenylacetylene (83% ee, 63% yield).