摘要
噁唑酮是合成α,α-二取代氨基酸、N,O-缩醛类化合物以及杂环化合物的重要前体,在有机合成中的应用越来越广泛.近年来基于噁唑酮的官能团转化合成了一系列重要有机化合物,特别是利用其不对称转化得到了重要手性化合物.因此,涉及噁唑酮转化的反应引起了越来越多科研工作者关注.基于噁唑酮多活性位点的特性,按其不同活性位点分类综述了噁唑酮参与的各种有机反应,包括C-2位、C-4位和C-5位官能团化以及多反应位点的环加成反应.同时也重点介绍了本课题组最近开发的基于邻苯二甲酰羟胺活性酯原位形成噁唑酮合成手性非天然氨基酸的方法,与已有的噁唑酮官能团化反应形成优势互补,促进该领域的蓬勃发展.最后对该领域所面临的挑战和机遇进行了展望和探讨.
Azlactones constitute a crucial precursor for the preparation ofα,α-disubstituted amino acids,N,O-acetal derivatives,many heterocyclic compounds,finding increasingly widespread applications in organic chemistry.Recent advances in functionalization of azlactone have enabled the synthesis of many important organic compounds.Notably,asymmetric transformations of azlactone have facilitated the preparation of valuable chiral compounds,attracting growing interest among researchers in this field.Focusing on the multi-active-site nature of azlactone,this review classifies its participation in diverse organic reactions,including C-2,C-4,and C-5 functionalization and multi-site cycloaddition reactions.Meanwhile,our research group has recently developed a novel method for the in situ formation of azlactones via the intramolecular cyclization of N-hydroxyphthalimide esters,which yields a various of chiral unnatural amino acids.This strategy complements existing azlactone functionalization reactions,thereby promoting the robust development of this field.Finally,the challenges and opportunities in this field are critically assessed,providing insights to direct future research and innovation.
作者
姜志洁
陈锦秀
朱晓菲
邓鑫浩
严琼姣
汪伟
周慧
Jiang Zhijie;Chen Jinxiu;Zhu Xiaofei;Deng Xinhao;Yan Qiongjiao;Wang Wei;Zhou Hui(College of Biology,Food and Chemistry,Shaanxi Xueqian Normal University,Xi'an 710100;College of Chemistry,Central China Normal University,Wuhan 430079;Pharmaceutical Research Institute,Wuhan Institute of Technology,Wuhan 430205;Pingwu High School,Mianyang,Sichuan 621000)
出处
《有机化学》
北大核心
2026年第1期1-20,共20页
Chinese Journal of Organic Chemistry
基金
湖北省自然科学基金(No.2025AFB675)
2024年度陕西高校优秀青年杰出人才支持计划(No.2025QJ-02(内))资助项目.
关键词
噁唑酮
活性位点
官能团化
氨基酸
不对称转化
azlactones
reactive site
functionalization
amino acids
asymmetric transformation
