Hetero Diels-Alder reactions (HDAR) of α,α′-dioxothiones on solid support |
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Authors: | Stefano Menichetti Mattia Mori Cristina Nativi |
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Institution: | Dipartimento di Chimica Organica ‘Ugo Schiff’, Polo Scientifico—Università di Firenze, via della Lastruccia 13, I-50019 Sesto Fiorentino (FI), Italy |
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Abstract: | Solid-supported α,α′-dioxothiones are easily obtained starting from β-ketoester modified Wang and hydroxymethylated polystyrene resins. The hetero Diels-Alder reactions (HDAR) of these species, used either as electron-poor dienes or dienophiles, followed by a simple cleavage of the products from the resin by trans-esterification with sodium methoxide, allowed the isolation of the desired cycloadducts in overall yields up to 90%. |
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Keywords: | Phthalimidesulfenyl chloride Dioxothiones Hetero Diels-Alder reactions Solid-phase synthesis Sulfur heterocycles |
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