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题名: Facile Synthesis of Chiral Spirooxindole-Based Isotetronic Acids and 5-1H-Pyrrol-2-ones through Cascade Reactions with Bifunctional Organocatalysts
作者: Guo, Wengang1;  Wang, Xu1;  Zhang, Boyu1;  Shen, Shuai1;  Zhou, Xin1;  Wang, Peng1;  Liu, Yan1;  Li, Can1
关键词: pyrrol-2-ones ;  cascade reactions ;  isatins ;  isotetronic acids ;  organocatalysis
刊名: CHEMISTRY-A EUROPEAN JOURNAL
发表日期: 2014-07-07
DOI: 10.1002/chem.201402945
卷: 20, 期:28, 页:8545-8550
收录类别: SCI ;  IC ;  CCR
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Multidisciplinary
研究领域[WOS]: Chemistry
英文摘要: Unprecedented organocatalyzed asymmetric cascade reactions have been developed for the facile synthesis of chiral spirooxindole-based isotetronic acids and 5-1H-pyrrol-2-ones. The asymmetric 1,2-addition reactions of alpha-ketoesters to isatins and imines by using an acid-base bifunctional 6'-OH cinchona alkaloid catalyst, followed by cyclization and enolization of the resulting adducts, gave chiral spiroisotetronic acids and 5-1H-pyrrol-2-ones, respectively, in excellent optical purities (up to 98% ee). FT-IR analysis supported the existence of hydrogen-bonding interaction between the 6'-OH group of the cinchona catalyst and an isatin carbonyl group, an interaction that might be crucial for catalyst activity and stereocontrol.
关键词[WOS]: ASYMMETRIC ALDOL REACTIONS ;  PROTEIN-PROTEIN INTERACTION ;  YEAST MALASSEZIA-FURFUR ;  MANNICH-TYPE REACTIONS ;  ENANTIOSELECTIVE SYNTHESIS ;  TERMINAL ALKYNOATES ;  CONJUGATE ADDITION ;  DERIVATIVES ;  ISATINS ;  INHIBITORS
语种: 英语
WOS记录号: WOS:000338768900005
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/145695
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, State Key Lab Catalysis, Dalian 116023, Peoples R China

Recommended Citation:
Guo, Wengang,Wang, Xu,Zhang, Boyu,et al. Facile Synthesis of Chiral Spirooxindole-Based Isotetronic Acids and 5-1H-Pyrrol-2-ones through Cascade Reactions with Bifunctional Organocatalysts[J]. CHEMISTRY-A EUROPEAN JOURNAL,2014,20(28):8545-8550.
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