Department of Chemistry, University of Colorado, Boulder, Colorado 80309, United States.
Org Lett. 2021 Jun 4;23(11):4289-4293. doi: 10.1021/acs.orglett.1c01035. Epub 2021 May 24.
Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These reactions are characterized by high anomeric selectivities for 2-deoxysugars and broad substrate scope (24 examples), including disaccharides and trifluoroborates with free hydroxyl groups. Taken together, this new class of carbohydrate reagents adds the palette of anomeric nucleophile reagents suitable for efficient installation of C-C bonds.
对端基碳原子的立体选择性反应是制备性碳水化合物化学的基础。在这里，我们报告了 BMIDA 酯衍生的端基三氟化硼的对映选择性 C-芳基化和醚化反应。这些反应的特点是 2-脱氧糖具有高的端基选择性，且底物范围广泛（24 个实例），包括二糖和带有游离羟基的三氟化硼。总的来说，这一类新的碳水化合物试剂增加了适用于高效安装 C-C 键的端基亲核试剂的种类。
