Mukherjee Debaraj, Yousuf Syed Khalid, Taneja Subhash Chandra
Bio-organic Chemistry Division, Indian Institute of Integrative Medicine (CSIR), Canal Road, Jammu, India-180001.
Org Lett. 2008 Nov 6;10(21):4831-4. doi: 10.1021/ol801917n. Epub 2008 Oct 4.
Lewis acid mediated one-pot transformation of D-glucal in the presence of nucleophiles leads to the formation of racemic alpha-substituted alpha-hydroxymethyl furfuryl derivatives, versatile synthons for biologically active molecules. Transformations using O-, S-, C-, and N-nucleophiles could be achieved readily under mild and scalable conditions. Indium triflate proved to be the catalyst of choice in terms of conversion and regioselectivity.
在亲核试剂存在下，路易斯酸介导的D-葡糖醛的一锅法转化导致形成外消旋α-取代的α-羟甲基糠基衍生物，这是用于生物活性分子的通用合成子。使用O-、S-、C-和N-亲核试剂的转化可以在温和且可扩展的条件下轻松实现。就转化率和区域选择性而言，三氟甲磺酸铟被证明是首选催化剂。
