手性相转移催化剂的研究进展——以金鸡纳碱与多种骨架手性相转移催化剂为例
Recent Advances in Chiral Phase-Transfer Catalysts—Taking Cinchona Alkaloids and Multiple Skeleton Chiral Phase-Transfer Catalysts as Examples
摘要: 手性相转移催化因反应条件温和、操作简便，已成为不对称合成中构建碳–碳及碳–杂原子键的重要策略。本文综述了以金鸡纳生物碱、联萘酚、酒石酸、胍类、三唑鎓盐、螺环骨架及手性季鏻盐为代表的手性相转移催化剂的研究进展。金鸡纳碱衍生催化剂历经四代发展，通过空间位阻与氢键调控实现高效立体控制；联萘骨架季铵盐(Maruoka催化剂)凭借C2对称性与刚性结构，可在超低用量下获得优异对映选择性；酒石酸、胍类、三唑鎓盐及螺环铵盐等新型催化剂通过氢键导向与手性空腔调控拓展了反应类型；手性季鏻盐因极化能力强、热稳定性高，在亲核加成等反应中展现出独特优势。尽管该领域已取得显著进展，但在催化剂精准设计、反应类型拓展及工业化应用等方面仍面临挑战。未来结合理论计算与人工智能辅助设计，发展多功能协同催化体系，将进一步推动手性相转移催化的广泛应用。
Abstract: Chiral phase-transfer catalysis has emerged as a pivotal strategy in asymmetric synthesis for constructing carbon-carbon and carbon-heteroatom bonds, owing to its mild reaction conditions and operational simplicity. This article reviews the research progress of chiral phase-transfer catalysts represented by cinchona alkaloids, binaphthols, tartaric acid derivatives, guanidines, triazolium salts, spirocyclic frameworks, and chiral quaternary phosphonium salts. Cinchona alkaloid-derived catalysts have undergone four generations of development, achieving efficient stereocontrol through the modulation of steric hindrance and hydrogen bonding. Binaphthyl-based quaternary ammonium salts (Maruoka catalysts), leveraging C₂ symmetry and rigid structures, deliver excellent enantioselectivity even at ultralow catalyst loadings. Emerging catalysts such as tartaric acid derivatives, guanidines, triazolium salts, and spirocyclic ammonium salts have expanded the scope of reactions through hydrogen-bonding guidance and chiral cavity modulation. Chiral quaternary phosphonium salts, characterized by high polarization ability and thermal stability, exhibit unique advantages in nucleophilic addition reactions. Despite significant progress in this field, challenges remain in the precise design of catalysts, expansion of reaction types, and industrial applications. Future efforts integrating theoretical calculations and artificial intelligence-assisted design to develop multifunctional cooperative catalytic systems will further promote the widespread application of chiral phase-transfer catalysis.
文章引用：田涛. 手性相转移催化剂的研究进展——以金鸡纳碱与多种骨架手性相转移催化剂为例[J]. 有机化学研究, 2026, 14(2): 323-339. https://doi.org/10.12677/jocr.2026.142029

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