Reeves Jonathan T, Lorenc Chris, Camara Kaddy, Li Zhibin, Lee Heewon, Busacca Carl A, Senanayake Chris H
Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road, P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.
J Org Chem. 2014 Jun 20;79(12):5895-902. doi: 10.1021/jo500848a. Epub 2014 Jun 4.
The addition of carbamoyl anions derived from N,N-disubstituted formamides and LDA to N-tert-butyl nitrones is described. The reaction was demonstrated with a variety of formamides and nitrones and provided a direct route to α-(N-hydroxy)amino amides. The use of a tert-leucinol derived chiral auxiliary on the nitrone provided products in good diastereoselectivity. Derivatization of the products by tert-butyl deprotection or N-deoxygenation was demonstrated.
本文描述了由N，N-二取代甲酰胺和LDA衍生的氨甲酰基阴离子与N-叔丁基硝酮的加成反应。该反应通过多种甲酰胺和硝酮得到了验证，并提供了一条直接合成α-（N-羟基）氨基酰胺的途径。在硝酮上使用叔亮氨酸衍生的手性助剂可提供具有良好非对映选择性的产物。还展示了通过叔丁基脱保护或N-脱氧对产物进行衍生化的方法。
