Application of Organocatalysis in Asymmetric Construction of Nitrogen-Containing Heterocyclic Compounds
Year: 2021
Type: article
Abstract: Nitrogen-containing heterocyclic structures are widely encountered in natural products and pharmaceuticals, which demonstrate broad-spectrum biological and pharmacological activities, and have attracted intensive attention from organic chemists and medicinal chemists.As a consequence, developing their green and efficient pathways, especially in asymmetric fashion, has always been a hot research field in the synthetic chemistry.In recent years, a series of organocatalysts based on amino acid such as proline and pyroglutamic acid have been reported, which have been well applied in the asymmetric construction of various nitrogen-containing compounds.This account mainly focuses on the research of asymmetric synthesis of nitrogen-containing heterocyclic compounds in our group, and the possible mechanisms of some typical reactions are thus discussed.Keywords organocatalysis; asymmetric synthesis; N-heterocycle; proline; pyroglutamic acid 含氮杂环化合物广泛存在于天然产物和药物分子 中 (Scheme 1) [1] , 如 Cipargamin [1c] , Martinellic [1d] 和 (-)-Alloaristoteline [1e] , 具有多种生物和药理活性.据统 计, 2015～2018 年期间, 美国食品药品监督管理局 (FDA)批准的小分子药物结构中 85%以上含有含氮杂环 骨架 [2] , 而且, 许多含氮杂环药物分子包含一个或多个 手性中心, 具有不同旋光活性的异构体在生物活性上通 常显示很大的差异性.例如, 广为人知的抗妊娠呕吐反 应药物沙利度胺, 因其对映异构体的致畸性作用导致现 代医学史上最大的灾难--反应停事件 [3] .再如, (R)-(-)-巴比妥是一种安眠药, 而其对映体会导致癫痫 [4] . 精准、快捷且绿色、高效地构建手性含氮杂环化合物对 药物开发具有非常重要的意义.2000 年以来, 在 MacMillan [5] 、List [6] 、邓力 [7] 、史 一安 [8] 、Jacobsen [9] 等国内外有机化学家们的推动下, 有 机小分子不对称催化
Authors: Yu Zheng, Zhenzhen Xie, Kai Chen,, Haoyue Xiang,, Hua Yang,
Institution: Central South University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4240560776