Laboratory of Organic Chemistry, Faculty of Pharmacy and Insitute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII, s/n, 08028 Barcelona, Spain.
Chemistry. 2011 Jul 4;17(28):7724-32. doi: 10.1002/chem.201100471. Epub 2011 Jun 10.
Phenylglycinol-derived, unsaturated oxazolopiperidone lactams are extremely useful building blocks that undergo stereoselective conjugate addition reactions with organocuprates, enolates, and sulfur-stabilized anions, allowing the stereocontrolled introduction of substituents at the piperidine 4-position. The factors governing the exo- or endo-facial selectivity are discussed. The methodology can be used for the preparation of a variety of enantiopure piperidines, including pharmaceuticals, alkaloids precursors, piperidine-fused derivatives, as well as complex piperidine-containing natural products.
苯甘氨醇衍生的不饱和噁唑烷酮内酰胺是非常有用的构建块，它们与有机铜试剂、烯醇盐和硫稳定的阴离子进行立体选择性共轭加成反应，允许在哌啶 4-位立体控制地引入取代基。讨论了控制外消旋或内消旋选择性的因素。该方法可用于制备各种手性纯哌啶，包括药物、生物碱前体、哌啶稠合衍生物以及复杂的含哌啶的天然产物。
