金鸡纳生物碱硫脲催化的螺[吡喃-3,3'-氧化吲哚]衍生物的对映选择性合成：水对映选择性有显著影响。
Enantioselective synthesis of spiro[-pyran-3,3'-oxindole] derivatives catalyzed by cinchona alkaloid thioureas: Significant water effects on the enantioselectivity.
作者信息
Konda Swapna, Jakkampudi Satish, Arman Hadi D, Zhao John C-G
机构信息
Department of Chemistry, University of Texas at San Antonio, One UTSA Circle, San Antonio, TX 78249-0698, USA.
出版信息
Synth Commun. 2019;49(21):2971-2982. doi: 10.1080/00397911.2019.1651866. Epub 2019 Aug 14.
Abstract
An efficient stereoselective three-component reaction for the synthesis of functionalized spiro[4-pyran-3,3'-oxindole] derivatives was realized through an organocatalyzed domino Knoevenagel/Michael/cyclization reaction using a cinchonidine-derived thiourea as the catalyst. Using water as the additive was found to improve the product ee values significantly. Under the optimized conditions, the reactions between isatins, malononitrile, and 1,3-dicarbonyl compounds yield the desired spirooxindole products in good yields (71-92%) and moderate to high ee values (up to 87% ee).
摘要
通过使用辛可尼定衍生的硫脲作为催化剂的有机催化多米诺Knoevenagel/迈克尔/环化反应，实现了一种高效的立体选择性三组分反应，用于合成功能化的螺[4-吡喃-3,3'-氧化吲哚]衍生物。发现使用水作为添加剂可显著提高产物的对映体过量值（ee值）。在优化条件下，异吲哚酮、丙二腈和1,3-二羰基化合物之间的反应以良好的产率（71-92%）和中等至高的ee值（高达87%ee）生成所需的螺氧化吲哚产物。
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