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| In the [2 + 2 + 2] cyclotrimerization (36¨C38) of diynes 4a,b,d using Grubbs¡¯ first-generation catalyst and propargyl alcohol (39), one significant difference in regioselectivity was noted in comparison to our original solution-phase results. While isoindolines 26a,d were formed in the expected regioselectivities (26a, 100¡Ã0; 26d/26¡äd, 50¡Ã50), the corresponding phenyl-substituted product 26b/26¡äb was formed in significantly lower regioselectivity on solid support (67¡Ã33 vs. 91¡Ã9).We again postulate that this difference may result from interactions of this aromatic substrate with the polystyrene matrix in the solid-phase reaction. Notably, however, this decreased selectivity was advantageous in this particular context, because it afforded access to the minor regioi-somer 26¡äb that was not accessible in useful quantities via the solution-phase reaction. |
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