本文選題：不對稱合成　切入點：螺環(huán)氧化吲哚γ-內(nèi)酯　出處：《有機化學(xué)》2017年10期

【摘要】：關(guān)于含三個手性中心的螺環(huán)氧化吲哚γ-內(nèi)酯的不對稱合成鮮有報道.丙醛和氧化吲哚烯烴首先經(jīng)有機催化進行不對稱Michael加成反應(yīng);隨后,在水/油兩相條件下,Michael加成物經(jīng)H_2O_2/K_2CO_3體系調(diào)節(jié),進行α-羥基化/半縮醛化的串聯(lián)反應(yīng);最后經(jīng)氯鉻酸吡啶(PCC)氧化,得到新穎的螺環(huán)氧化吲哚α-甲基仲康酸酯化合物.該合成策略具有條件溫和、收率高(91%~98%)、對映選擇性優(yōu)秀(87%~95%)的特點,為手性多取代的螺環(huán)氧化吲哚γ-內(nèi)酯的合成提供了一種簡易的新方法.所有新產(chǎn)物均通過核磁共振譜和高分辨質(zhì)譜對其結(jié)構(gòu)進行確證.
[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 偽 -hydroxylation / semi-acetalization reaction was carried out in series. Finally, the adducts were oxidized by pyridine chloride chromate. A novel compound of indole 偽 -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).
【作者單位】： 浙江工業(yè)大學(xué)催化加氫研究中心浙江省綠色農(nóng)藥清潔生產(chǎn)技術(shù)研究重點實驗室;
【基金】：國家自然科學(xué)基金(No.21402176)資助項目~~
【分類號】：O626

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