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Catalytic Asymmetric Construction of 3,3 '-Spirooxindoles Fused with Seven-Membered Rings by Enantioselective Tandem Reactions

机译:对映选择性串联反应催化不对称结构的3,3'-螺氧基吲哚与七元环融合。

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摘要

The first catalytic asymmetric construction of a spirooxindole scaffold incorporated with a seven-membered benzodiazepine moiety has been established by a three-component (isatin, 1,2-phenylenediamine, cyclohexane-1,3-dione) tandem reaction catalyzed by a chiral phosphoric acid. Structurally complex spirobenzodiazepine oxindoles with one quaternary stereogenic center are obtained in high yield with excellent enantioselectivity (up to 99% yield, enantiomeric ratio>99.5:0.5). This approach takes advantage of organocatalytic asymmetric tandem reactions to efficiently construct the structurally rigid spirobenzodiazepine oxindole architecture with high enantiopurity in a single transformation, which involves a cascade enamine-imine formation/intramolecular Mannich reaction sequence.
机译:通过手性磷酸催化的三组分串联反应(isatin,1,2-苯二胺,环己烷-1,3-dione),建立了掺有七元苯并二氮杂moiety基的螺并吲哚骨架的第一个催化不对称结构。 。具有高收率和优异的对映选择性(高达99%收率,对映体比率> 99.5:0.5),可高收率地获得结构复杂的具有一个季生立体中心的螺苯并二氮杂pine吲哚。该方法利用有机催化不对称串联反应的优势,通过一次转化即可高效构建具有高对映体纯度的结构刚性螺二苯并二氮杂卓吲哚结构,涉及级联烯胺-亚胺形成/分子内曼尼希反应序列。

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