Photochemical Rearrangement of <i>N</i>-Chlorolactams: A Route to <i>N</i>-Heterocycles through Concerted Ring Contraction
作者:Dana K. Winter、Alexandre Drouin、Jean Lessard、Claude Spino
DOI:10.1021/jo100181h
日期:2010.4.16
We report a novel ring contraction allowing the direct conversion of N-chlorolactams to their corresponding ring-contraction N-heterocycles upon photolysis. Results show that the rearrangement occurs with a variety of N-chlorolactams and that the greater the substitution at the migrating carbon, the greater the yield of product. Importantly, stereochemistry at the migrating carbon is conserved in the
我们报道了一种新颖的环收缩,其允许N-氯内酰胺在光解后直接转化为其相应的环收缩N-杂环。结果表明,各种N-氯内酰胺都发生了重排,并且在迁移的碳上取代量越大,产物的收率就越高。重要的是,产物中保留了迁移碳处的立体化学。分离出重排产物,其为氨基甲酸甲酯,收率从17%到58%不等,主要副产物为可回收的母体内酰胺。