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题名: Chiral Phosphoric Acid Catalyzed Asymmetric Ugi Reaction by Dynamic Kinetic Resolution of the Primary Multicomponent Adduct
作者: Zhang, Yun1; Ao, Yu-Fei1; Huang, Zhi-Tang1; Wang, De-Xian1; Wang, Mei-Xiang2; Zhu, Jieping3
关键词: asymmetric synthesis ; kinetic resolution ; multicomponent reaction ; organocatalysis ; reaction mechanisms
刊名: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
发表日期: 2016-04-18
卷: 55, 期:17, 页:5282-5285
收录类别: SCI
英文摘要: Reaction of isonitriles with 3-(arylamino)isobenzofuran-1(3H)-ones in the presence of a catalytic amount of an octahydro (R)-binol-derived chiral phosphoric acid afforded 3-oxo-2-arylisoindoline-1-carboxamides in high yields with good to high enantioselectivities. An enantioselective Ugi four-center three-component reaction of 2-formylbenzoic acids, anilines, and isonitriles was subsequently developed for the synthesis of the same heterocycle. Mechanistic studies indicate that the enantioselectivity results from the dynamic kinetic resolution of the primary Ugi adduct, rather than from the C-C bond-forming process. The resulting heterocycle products are of significant medicinal importance.
语种: 英语
内容类型: 期刊论文
URI标识: http://ir.iccas.ac.cn/handle/121111/36021
Appears in Collections:分子识别与功能实验室_期刊论文

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作者单位: 1.Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
2.Tsinghua Univ, Key Lab Bioorgan Phosphorous & Chem Biol, Minist Educ, Beijing 100184, Peoples R China
3.Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Synth & Nat Prod, EPFL SB ISIC LSPN,BCH 5304, CH-1015 Lausanne, Switzerland
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