POLYMER-SUPPORTED PREPARATION OF SUBSTITUTED PHENOLS - A NEW EXAMPLE OF SIMULTANEOUS CYCLIZATION-CLEAVAGE REACTION ON SOLID-PHASE

A series of variously substituted phenols was synthesized in high yiel ds using the ''cyclization-cleavage'' approach. Base-catalyzed reactio ns between cr,P-unsaturated ketones and polymer-bound acetonyl groups result in a tandem Michael addition/annulation reaction followed by el imination 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 impuritie s. This efficient one-pot aromatic ring formation represents a new var iant of solid phase synthesis. (C) 1998 Elsevier Science Ltd. All righ ts reserved.