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Synfacts 2008(3): 0323-0323
DOI: 10.1055/s-2008-1042676
DOI: 10.1055/s-2008-1042676
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Solid-Phase Synthesis of Diverse α,β-Unsaturated Carbonyl Compounds
Y.-F. Chang, Y.-R. Jiang, W.-C. Cheng*
The Genomics Research Center, Taipei, Taiwan
Further Information
Publication History
Publication Date:
21 February 2008 (online)
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).