7878
selectivity, high chemical purity, easy recovery and recycling of the starting resin. Applications
of this methodology to the synthesis of various substituted olefinic compounds is currently under
investigation.
References
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S. R. Tetrahedron Lett. 1997, 38, 4021–4024; (c) Winkler, J. D.; McCoull, W. Tetrahedron Lett. 1998, 39,
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B. Tetrahedron Lett. 1996, 37, 8151–8154; (c) Tietze, L. F.; Hippe, T.; Steinmetz, A. Synlett 1996, 1043–1044; (d)
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6. Caution! The bromide 4 is a highly allergenic compound.
7. Merrifield resin (200–400 mesh) from Fluka crosslinked with 1% of DVB; loading 0.8 mmol Cl/g.
8. Loev, B.; Dawson, C. R. J. Am. Chem. Soc. 1956, 78, 6095–6098.
9. Selected 13C MAS NMR (100.7 MHz; CDCl3) data: 1 l 141.5, 129.8, 114.9, 110.3, 106.1, 70.1, 33.7; 9 l 188.1,
171.7, 157.7, 151.5, 145.2, 143.1, 131.2, 114.4, 97.8, 96.0, 82.6, 69.9, 62.1, 61.6, 34.8, 15.1.
10. Gorgues, A.; Stephan, D.; Belyasmine, A.; Khanous, A.; Le Coq, A. Tetrahedron 1990, 46, 2817–2826.
11. Gustafsson, J.; Sterner, O. J. Org. Chem. 1994, 59, 3994–3997.
12. This reaction is extremely air-sensitive: when the same reaction was run under argon in a round-bottomed flask
equipped with a condenser using a toluenic solution where argon was previously bubbled, we found only
polymeric compounds and the product resulting from Michael addition of furan 5 to the ynal 7.
.
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