Cyclic sulfates as useful tools in the asymmetric synthesis of 1-aminocyclopropane-1-carboxylic acid derivatives
作者:Anna Jakubowska、Grzegorz Żuchowski、Katarzyna Kulig
DOI:10.1016/j.tetasy.2015.09.013
日期:2015.12
2-dioxathiolane-2,2-dioxide and 4-(methoxymethyl)-1,3,2-dioxathiolane-2,2-dioxide have been used as ‘epoxide-like’ synthons during the asymmetric alkylation of oxazinone-derived glycine equivalents. Using a fully stereoselective synthesis, eight stereoisomers of the spiro derivatives of the glycine equivalents were obtained. The relative configurations of the spiro compounds obtained were easily determined
4-(2-甲氧基乙基)-1,3,2-二氧杂硫杂环戊烷-2,2-二氧化物和4-(甲氧基甲基)-1,3,2-二氧杂硫杂环戊烷-2,2-二氧化物的对映体已被用作'环氧化物恶嗪酮衍生的甘氨酸当量的不对称烷基化过程中的“类”合成子。使用完全立体选择性合成,所述的立体异构体8螺获得甘氨酸当量的衍生物。所述的相对构型螺得到的容易使用核磁共振光谱和二维核Overhauser效应实验确定的化合物。此外,的将在S毗卢 将获得的衍生物水解为相应的氨基酸,该氨基酸为1-氨基环丙烷-1-羧酸的衍生物,1-氨基环丙烷-1-羧酸是许多化合物中存在的非常重要的结构单元,具有令人感兴趣的生物学活性。