Solid-supported a,a0-dioxothiones are easily obtained starting from b-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%.
Inverse Electron Demand Hetero Diels-Alder Reactions of Solid Supported alpha-Acilthiones / S. Menichetti; M. Mori; C. Nativi. - In: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS. - ISSN 1042-6507. - STAMPA. - 180:(2005), pp. 1327-1331.
Inverse Electron Demand Hetero Diels-Alder Reactions of Solid Supported alpha-Acilthiones
MENICHETTI, STEFANO
;NATIVI, CRISTINA
2005
Abstract
Solid-supported a,a0-dioxothiones are easily obtained starting from b-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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