Rouh Hossein, Tang Yao, Xu Ting, Yuan Qingkai, Zhang Sai, Wang Jia-Yin, Jin Shengzhou, Wang Yu, Pan Junyi, Wood Hannah L, McDonald James D, Li Guigen
Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, Texas 79409-1061, USA.
Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China.
Research (Wash D C). 2022 Aug 11;2022:9865108. doi: 10.34133/2022/9865108. eCollection 2022.
A new chiral aggregate-based tool for asymmetric synthesis has been developed by taking advantage of chiral aggregates of GAP (Group-Assisted Purification) reagents, -phosphonyl imines. This tool was proven to be successful in the asymmetric GAP synthesis of functionalized 2,3-dihydrobenzofurans by reacting salicyl -phosphonyl imines with dialkyl bromomalonates in various cosolvent systems. The chiral induction can be controlled by differentiating between two asymmetric directions simply by changing the ratios of cosolvents which are commonly adopted in AIE (aggregation-induced emission) systems. The formation of chiral aggregates was witnessed by a new analytical tool-aggregation-induced polarization (AIP). The present synthetic method will be broadly extended for general organic synthesis, particularly, for asymmetric synthesis and asymmetric catalysis in the future.
利用GAP（基团辅助纯化）试剂的手性聚集体——磷酰亚胺，开发了一种用于不对称合成的基于新型手性聚集体的工具。通过使水杨醛磷酰亚胺与二烷基溴代丙二酸酯在各种共溶剂体系中反应，该工具在功能化2,3-二氢苯并呋喃的不对称GAP合成中被证明是成功的。通过简单地改变AIE（聚集诱导发光）体系中常用的共溶剂比例，可以区分两个不对称方向来控制手性诱导。一种新的分析工具——聚集诱导极化（AIP）证实了手性聚集体的形成。目前的合成方法将在未来广泛应用于一般有机合成，特别是不对称合成和不对称催化。
