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Synfacts 2006(4): 0403-0403
DOI: 10.1055/s-2006-932085
DOI: 10.1055/s-2006-932085
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York
Polymer-Supported Acetylenic Sulfones
T. G. Back*, H. Zhai
University of Calgary, Canada
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
24. März 2006 (online)
Significance
Acetylenic sulfones were anchored onto the Merrifield resin by an ester linker. Sulfonhydrazide 1 was converted into selenosulfonate 2, followed by free radical selenosulfonation of actylenes to give adducts 3a-c. Esterification of resin 4 with 3a-c afforded the desired products 5a-c, respectively. Desilylation of 5c gave the terminal acetylene 5d. Resins 5a,b,d were subjected to a variety of cyclization and cycloaddition reactions with chloroamines 6 and 7, cyclopentadiene 8, and nitrile N-oxide 9 to give the corresponding cycloadducts (17 examples, 34-100% yield).