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Synfacts 2007(12): 1324-1324  
DOI: 10.1055/s-2007-991392
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Immobilization of Pybox Ligand to Polystyrene Resin via Click Chemistry

Contributor(s): Yasuhiro Uozumi, Yohei Oe
M. Tilliet, S. Lundgren, C. Moberg, V. Levacher*
Université et INSA de Rouen, Mont-Saint-Aignan, France and KTH School of Chemical Science and Engineering, Stockholm, Sweden
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Publication History

Publication Date:
22 November 2007 (online)

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Significance

Polystyrene-supported Ph-pybox ligand was prepared via click chemistry and applied to asymmetric catalyses. Thus, the Sonogashira reaction of 4-bromo-substituted Ph-pybox 1 with (trimethylsilyl)acetylene 2 in the presence of palladium catalyst gave 4-[(tri­methylsilyl)ethynyl]-pybox 3 (eq. 1). After removal of the TMS group with TBAF, click reaction of the resulting pybox 4, bearing a terminal alkyne, with polystyrene-supported azide 5 in the presence of CuI catalyst afforded the polystyrene-supported Ph-pybox 6. Enantioselective alkynylation of imines 7 with phenylacetylene 8 was carried out in the presence of CuOTf and 6 to give the corresponding propargylic amines 9 in 73-100% conversion with 80-90% ee.