Solid-Phase Synthesis of Diverse α,β-Unsaturated Carbonyl Compounds

Significance

Polymer-bound sulfones 2 were prepared by treatment of polystyrene benzene­sulfinate 1 with benzyl bromides. The reaction of 2 with dimsyl anion as a base followed by addition of allyl bromides gave the corresponding resins 3. These resins (R² = H, Me; R³ = H, Me) were transformed to the corresponding α,β-carbonyl compounds 5 via ozonolysis and β-elimination cleavage in 77-96% overall yields with 85-95% purity from resin 1 (12 compounds). To increase the library diversity, resin 3 (R³ = Br) was transformed to 5, bearing various R³ substituents, via solid-phase Suzuki-coupling reactions followed by the cleavage in 70-88% overall yields with 85-95% purity (four compounds).