Polymer-supported preparation of substituted phenols: A new example of simultaneous cyclization-cleavage reaction on solid phase

Article abstract of DOI:10.1016/S0040-4039(98)01771-7

A series of variously substituted phenols was synthesized in high yields using the 'cyclization-cleavage' approach. Base-catalyzed reactions between α,β-unsaturated ketones and polymer-bound acetonyl groups result in a tandem Michael addition/annulation reaction followed by elimination and rearrangement into phenols. Since all intermediates are on the resin until the last stage, the final reaction products contain only the desired phenols with the starting ketones as minor impurities. This efficient one-pot aromatic ring formation represents a new variant of solid phase synthesis.