Department of Drug and Natural Product Synthesis, Faculty of Life Sciences, University of Vienna, Althanstrasse 14, Vienna, A-1090, Austria.
Chem Commun (Camb). 2013 Sep 28;49(75):8383-5. doi: 10.1039/c3cc44255a.
The addition of lithium carbenoids to isocyanates provides a versatile access to N-substituted 2-haloacetamides: the reaction tolerates the presence of variously functionalized substituents on the nitrogen atom, including sterically demanding ones and reactive halogens. No erosion of the enantiopurity was observed in the case of optically active isocyanates. One of the substrates prepared has been employed in Charette's type chemoselective addition of a Grignard reagent to access an α-chloroketone.
锂碳烯加成到异氰酸酯上为 N-取代的 2-卤代乙酰胺提供了一种通用的合成方法：该反应可以容忍氮原子上各种官能团取代基的存在，包括空间位阻较大的取代基和反应性卤素。在光学活性异氰酸酯的情况下，没有观察到对映纯度的降低。所制备的底物之一已被用于 Charette 型选择性格氏试剂加成到α-氯代酮中。
