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Synfacts 2005(3): 0364-0364  
DOI: 10.1055/s-2005-921607
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Solid-Phase Enyne Metathesis Using Ruthenium Pre-catalysts

Contributor(s): Yasuhiro Uozumi, Maki Minakawa
D. E. A. Brittain, B. L. Gray, S. L. Schreiber*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
22 November 2005 (online)

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Significance

Treatment of polystyrene-bound 1-(3-{[diisopropylsilyl)oxy]phenyl}but-3-en-1-ol (1) with 7.5 equivalents of propynylboronate 4 in toluene in the presence ruthenium carbene complexes at 80 °C for 24 hours afforded annulation product 3. Ruthenium complex 2 (the so called Hoveyda-Grubbs pre-catalyst) was found to promote the solid-phase metathesis to form 3 (86% conversion), showing superior results compared to Grubbs’ 1st and 2nd generation pre-catalysts (15% and 33% conversion, respectively).