Duttwyler Simon, Chen Shuming, Lu Colin, Mercado Brandon Q, Bergman Robert G, Ellman Jonathan A
Department of Chemistry, Yale University, 225 Prospect St., New Haven, CT 06520 (USA).
Angew Chem Int Ed Engl. 2014 Apr 7;53(15):3877-80. doi: 10.1002/anie.201310517. Epub 2014 Mar 6.
The first example of C alkylation of 1,2-dihydropyridines with alkyl triflates and Michael acceptors was developed to introduce quaternary carbon centers with high regio- and diastereoselectivity. Hydride or carbon nucleophile addition to the resultant iminium ion also proceeded with high diastereoselectivity. Carbon nucleophile addition results in an unprecedented level of substitution to provide piperidine rings with adjacent tetrasubstituted carbon atoms.
开发了首例1,2 - 二氢吡啶与三氟甲磺酸烷基酯及迈克尔受体的C - 烷基化反应,以高区域和非对映选择性引入季碳中心。所得亚胺离子与氢化物或碳亲核试剂的加成反应也具有高非对映选择性。碳亲核试剂的加成导致了前所未有的取代水平,从而提供了带有相邻四取代碳原子的哌啶环。