Solid-phase synthesis of optically active substituted 2-aminofuranones using an activated carbonate linker
An efficient three-step solid-phase synthesis of diverse 3,5-disubstituted-2-aminofuranones has been developed. α-Hydroxy acids loaded on a nitrophenyl carbonate derivative of Wang resin are used as acylating agents for the C-acylation of active methylene
Matiadis, Dimitris,Prousis, Kyriakos C.,Igglessi-Markopoulou, Olga
A novel access to 2-aminofuranones via cyclization of functionalized γ-hydroxy-α,β-butenoates derived from N-hydroxybenzotriazole esters of α-hydroxy acids
The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of γ-hydroxy-functionalized butenoates which are cyclized under mild conditions to the corresponding 2-amino-3,5-disubstituted-4-furanones. That the products are optically active is confirmed by measurements of their optical rotations. On the other hand, replacement of N-hydroxybenzotriazole by N-hydroxysuccinimide might lead to by-products depending on the functionalized glycolic acid used.
Athanasellis, Giorgos,Detsi, Anastasia,Prousis, Kyriakos,Igglessi-Markopoulou, Olga,Markopoulos, John