Solid-Supported Cross-Metathesis

Significance

The cross-metathesis reaction of the Wang resin supported olefins 1a-c with external olefins 2 (excess) was catalyzed by the ruthenium carbene complexes 10 or 11 to give the corresponding products 3, 6, and 8. The treatment of the products with TFA, followed by the esterification with diazomethane gave the desired olefin products 4, 7, and 9. In the reaction of relatively flexible linear olefin 1a, the undesired side product 5 was also generated presumably via the intra-resin metathesis. In contrast, the reactions of 1b and 1c did not give the undesired products.