Innovation Research Center of Chiral Drugs, Institute for Advanced Study, Chengdu University, Chengdu, China.
Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, China.
Chirality. 2022 Jul;34(7):1019-1034. doi: 10.1002/chir.23455. Epub 2022 May 6.
A readily available chiral cyclohexanediamine-derived bifunctional tertiary amine-squaramide catalyst is more effective for the asymmetric dearomative 1,3-dipolar cycloaddition of 2-nitrobenzofurans and N-2,2,2-trifluoroethylisatin ketimines. A range of structurally diverse spiro-fused polyheterocyclic compounds containing oxindole, pyrrolidine, and hydrobenzofuran motifs were smoothly obtained in excellent results (up to 99% yield, >20:1 dr in all cases and up to 99% ee). This method features high efficiency, mild reaction conditions, exquisite asymmetric induction, wide functional group tolerance, great potential for scale-up synthesis, and attractive product diversification.
一种现成的手性环己二胺衍生双功能叔胺-酰亚胺催化剂对于 2-硝基苯并呋喃和 N-2,2,2-三氟乙基亚氨酸酮亚胺的不对称去芳构化 1,3-偶极环加成反应更为有效。一系列结构多样的螺稠合多杂环化合物，包含吲哚酮、吡咯烷和氢化苯并呋喃结构单元，以优异的结果（高达 99%的产率，所有情况下>20:1 的 dr，最高可达 99%的 ee）顺利获得。该方法具有高效、温和的反应条件、精湛的不对称诱导、广泛的官能团耐受性、大规模合成的巨大潜力和有吸引力的产物多样化。
