发展了一种以果糖衍生物为手性辅基,高立体选择性合成(1S)-反式一环丙烷衍生物的方法。将手性辅基丙烯酰化再与叔胺反应生成铵盐,用碳酸铯处理生成叶立德中间体,引发环丙烷化反应。本论文提供了一种有效合成二取代或多取代手性环丙烷的方法。
A new procedure for the highly diastereoselective synthesis of (1S)-trans-cyclopropane derivatives using a fructose derivative as the chiral auxiliary was developed. Chloroacetylated 1,2;4,5-di-O-isopropylidene-D-fructopyranose was reacted with a tertiary amine to form the ammonium salt, which was treated with cesium carbonate to give the cyclopropane derivative through ylide intermediate. The described procedure provides an efficient method to synthesize optically pure dior poly-substituded cyclopropanes.