Key Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen, China.
Org Lett. 2013 Apr 19;15(8):1958-61. doi: 10.1021/ol4006129. Epub 2013 Apr 8.
Highly functionalized pyrrolidine and piperidine analogues, with up to three stereogenic centers, were synthesized in good yield (50-95%), excellent dr (single isomer), and high ee (>90%) using a Cinchona alkaloid-derived carbamate organocatalyst. High stereoselective synergy was achieved by combining a reversible aza-Henry reaction with a dynamic kinetic resolution (DKR)-driven aza-Michael cyclization. Whereas both reactions proceed with moderate enantioselectivities (50-60% for each step), high enantioselectivities are obtained for the overall products devoid of dr sacrifice.
高功能化的吡咯烷和哌啶类似物，具有多达三个手性中心，使用金鸡纳生物碱衍生的氨基甲酸酯有机催化剂以良好的收率（50-95%）、优异的 dr（单一异构体）和高 ee（>90%）合成。通过将可逆的氮杂 Henry 反应与动态动力学拆分（DKR）驱动的氮杂 Michael 环化相结合，实现了高立体选择性协同作用。虽然这两个反应的对映选择性中等（每个步骤为 50-60%），但对于没有 dr 牺牲的整体产物，获得了高对映选择性。
