Rahman Md Ataur, Rehan Mohammad, Cellnik Torsten, Ahuja Brij Bhushan, Healy Alan R
Chemistry Program, New York University Abu Dhabi (NYUAD), Saadiyat Island, United Arab Emirates.
Org Lett. 2024 Oct 25;26(42):9040-9045. doi: 10.1021/acs.orglett.4c03251. Epub 2024 Oct 10.
Herein, we report the application of a benzyloxy-functionalized malonic acid half thioester as an activated ester equivalent in a highly enantioselective decarboxylative glycolate aldol reaction. This robust method operates at ambient temperature, tolerates air and moisture, and generates CO as the only byproduct. The synthetic applicability of the method is demonstrated by the large-scale enantiodivergent synthesis of α-benzyloxy-β-hydroxybutyric acid thioester and its subsequent conversion to diverse polyoxygenated building blocks, deoxy-sugars, and (-)-angiopterlactone B.
在此，我们报道了一种苄氧基官能化的丙二酸半硫酯作为活化酯等价物在高度对映选择性脱羧乙醇酸酯羟醛反应中的应用。这种稳健的方法在环境温度下操作，耐受空气和湿气，并产生一氧化碳作为唯一的副产物。该方法的合成适用性通过α-苄氧基-β-羟基丁酸硫酯的大规模对映发散合成及其随后转化为多种多氧化结构单元、脱氧糖和(-)-观音座莲内酯B得以证明。
