Sulfur dioxide-mediated syntheses of polyfunctional alkenes and (E,Z)- and (E,E)-2,4-dien-1-ones
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Homochiral Diels-Alder adduct of 2,4-dimethylfuran to 1-cyanovinyl (1'R)- or (1'S)-camphanate are transformed readily into polypropionate fragments containing four or five contiguous stereogenic centres. They can be condensed via cross-aldolizations to lit ...
In the presence of a Lewis or protic acid and at low temperature, 1,3-dioxy-1,3-dienes add to sulfur dioxide generating zwitterionic intermediates that can react with carbon nucleophiles such as allylsilanes. After a retro-ene elimination of SO2, valuable ...
