C O M M U N I C A T I O N S
Scheme 2. GH-II-Catalyzed 1,5-Enyne Metathesis: Scope
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Scheme 3. A Double 1,5-Enyne RCM
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Scheme 4.
of the Cookson’s reagent (4-phenyl-4,5-dihydro-3H-1,2,4-triazole-
3,5-dione, 5),14 cyclobutene 2a reacts at room temperature, to give
the tricyclic compound 6 in 80% yield and as a single diastereomer
(Scheme 4). An anti configuration was assigned, based on NOESY
experiments (see Supporting Information).
In conclusion, we have shown that Grubbs-type catalysts are able
to promote enyne metathesis on 1,5-enyne substrates, thus opening
a convenient new entry to functionalized cyclobutenes. Further
investigations on this reaction and functionalization of the cy-
clobutenes are ongoing and will be reported on due course.
(10) For a recent review on the synthesis of substituted cyclobutenes, see:
Gauvry, N.; Lescop, C.; Huet, F. Eur. J. Org. Chem. 2006, 5207-5218.
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H.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 7414-7415. (c) Hong,
S. H.; Wenzel, A. G.; Salguero, T. T.; Day, M. W.; Grubbs, R. H. J. Am.
Chem. Soc. 2007, 129, 7961-7968.
Acknowledgment. We are grateful to the CNRS for financial
support (ATIPE jeune e´quipe), and the Institut de Chimie des
Substances Naturelles (Gif sur Yvette) for a grant (O.D.).
(12) Kappe, C. O. Angew. Chem., Int. Ed. 2004, 43, 6250-6284.
Supporting Information Available: Experimental details and
characterization for all new compounds. This material is available free
(13) (a) Luzung, M. R.; Markham, J. P.; Toste, F. D. J. Am. Chem. Soc. 2004,
126, 10858-10859. (b) Georgy, M.; Boucard, V.; Campagne, J.-M. J.
Am. Chem. Soc. 2005, 127, 14180-14181.
(14) (a) Virolleaud, M.-A.; Piva, O. Eur. J. Org. Chem. 2007, 1606-1612.
(b) Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. Tetrahedron Lett.
1962, 3, 615-618.
References
(1) For a special issue dedicated to olefin metathesis, including Grubbs,
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issues 1-2.
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