Asymmetric Synthesis of 3-Spiro-Fused 2-Oxindoles via Organocatalyst/​N-Iodosuccinimide/Hydrogen Peroxide-Mediated Oxidative Cyclization.

IF 1.5 4区 医学 Q4 CHEMISTRY, MEDICINAL
Kosuke Nakashima, Yuichi Okuaki, Misaki Deguchi, Yasuyuki Matsushima, Shin-Ichi Hirashima, Tsuyoshi Miura
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引用次数: 0

Abstract

A squaramide organocatalyst was employed to efficiently promote asymmetric oxidative lactonization to construct spiro-fused 2-oxindoles in moderate-to-good yield and enantioselectivity (up to 81% enantiomeric excess (ee)). Herein, we report the first study accomplishing stereoselective oxidative cyclization from indole propionic acid using an organocatalyst, N-iodosuccinimide (NIS), and hydrogen peroxide under metal-free and mild reaction conditions.

有机催化剂/ n -碘丁二酰亚胺/过氧化氢催化氧化环化不对称合成3-螺融合2-氧吲哚。
采用方酰胺有机催化剂有效地促进不对称氧化内酯化反应,以中高收率和对映体选择性(高达81%的对映体过量(ee))构建螺体融合的2-氧吲哚。在此,我们首次报道了在无金属和温和的反应条件下,用有机催化剂n -碘丁二酰亚胺(NIS)和过氧化氢完成吲哚丙酸立体选择性氧化环化的研究。
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来源期刊
CiteScore
3.20
自引率
5.90%
发文量
132
审稿时长
1.7 months
期刊介绍: The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.
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