不对称高效构筑新颖螺环氧化吲哚α-甲基仲康酸酯

发布时间：2018-03-23 22:32

本文选题：不对称合成　切入点：螺环氧化吲哚γ-内酯　出处：《有机化学》2017年10期

【摘要】：关于含三个手性中心的螺环氧化吲哚γ-内酯的不对称合成鲜有报道.丙醛和氧化吲哚烯烃首先经有机催化进行不对称Michael加成反应;随后,在水/油两相条件下,Michael加成物经H_2O_2/K_2CO_3体系调节,进行α-羟基化/半缩醛化的串联反应;最后经氯铬酸吡啶(PCC)氧化,得到新颖的螺环氧化吲哚α-甲基仲康酸酯化合物.该合成策略具有条件温和、收率高(91%~98%)、对映选择性优秀(87%~95%)的特点,为手性多取代的螺环氧化吲哚γ-内酯的合成提供了一种简易的新方法.所有新产物均通过核磁共振谱和高分辨质谱对其结构进行确证.
[Abstract]:The asymmetric synthesis of indole-lactone with three chiral centers is rarely reported. Propionaldehyde and oxindolene are first catalyzed by organic catalysis for asymmetric Michael addition. Under the water / oil two-phase condition, the H_2O_2/K_2CO_3 system was used to regulate the adducts, and the 伪 -hydroxylation / semi-acetalization reaction was carried out in series. Finally, the adducts were oxidized by pyridine chloride chromate. A novel compound of indole 伪 -methyl-secondary acid ester was obtained. The synthetic strategy was characterized by mild conditions, high yield of 91H ~ (98), excellent enantioselectivity and excellent enantioselectivity. A new and simple method for the synthesis of chiral polysubstituted indole-indole-lactone was proposed. All the new products were characterized by NMR and high resolution mass spectrometry (HRMS).
【作者单位】：浙江工业大学催化加氢研究中心浙江省绿色农药清洁生产技术研究重点实验室;
【基金】：国家自然科学基金(No.21402176)资助项目~~
【分类号】：O626

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