Enantioselective intramolecular crossed rauhut-currier reactions through cooperative nucleophilic activation and hydrogen-bonding catalysis: Scope and mechanistic insight

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成果类型：

期刊论文

作者：

Wang, Xu-Fan;Peng, Liang;An, Jing;Li, Chao;Yang, Qing-Qing;...

通讯作者：

Gu, Feng-Long

作者机构：

[Wang, Xu-Fan; Yang, Qing-Qing; Lu, Liang-Qiu; Xiao, Wen-Jing; Li, Chao; An, Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Hubei, Peoples R China.

[Peng, Liang; Gu, Feng-Long] S China Normal Univ, Ctr Computat Quantum Chem, Guangzhou 510009, Guangdong, Peoples R China.

[Gu, Feng-Long] S China Normal Univ, Ctr Computat Quantum Chem, W 55 Zhongshan Rd, Guangzhou 510009, Guangdong, Peoples R China.

通讯机构：

[Gu, Feng-Long] S

S China Normal Univ, Ctr Computat Quantum Chem, W 55 Zhongshan Rd, Guangzhou 510009, Guangdong, Peoples R China.

语种：

英文

关键词：

asymmetric catalysis;cascade reactions;hydrogen bonds;Michael addition;Rauhut-Currier reaction

期刊：

CHEMISTRY-A EUROPEAN JOURNAL

ISSN：

0947-6539

年：

2011

卷：

期：

页码：

6484-6491

DOI：

10.1002/chem.201100479

基金类别：

National Science Foundation of ChinaNational Natural Science Foundation of China (NSFC) [20872043, 21072069, 21002036]; National Basic Research Program of ChinaNational Basic Research Program of China [2011CB808600]; Program for Changjiang Scholars and Innovative Research Team in UniversityProgram for Changjiang Scholars & Innovative Research Team in University (PCSIRT) [IRT0953]

机构署名：

本校为第一机构

院系归属：

化学学院

摘要：

A highly efficient and enantioselective intramolecular crossed Rauhut-Currier (RC) reaction of nitroolefins with tethered enonates has been developed through cooperative nucleophilic activation and a hydrogen-bonding catalytic strategy (≤98% ee and 98% yield). The reaction features simple experimental procedures and is completely chemoselective and atom-economic in character. The potential synthetic applications have been demonstrated by the conversion of the RC reaction products into biologically and pharmaceutically valuable compounds with h...

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Enantioselective intramolecular crossed rauhut-currier reactions through cooperative nucleophilic activation and hydrogen-bonding catalysis: Scope and mechanistic insight

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