Silicon-Based Bulky Group-Induced Remote Control and Conformational Preference in the Synthesis and Application of Isolable Atropisomeric Amides with Secondary Alcohol or Amine Moieties | |
Department | OSSO国家重点实验室 |
Bai XF(柏惺峰)1,2,3; Deng, Wen-Hui3; Xu, Zheng3; Li FW(李福伟)1,2; Deng, Yuan3; Xia CG(夏春谷)1,2; Xu LW(徐利文)1,2,3; Xia CG(夏春谷); Xu LW(徐利文) | |
2014 | |
Source Publication | Chemistry - An Asian Journal |
ISSN | 1861-4728 |
Volume | 9Issue:4Pages:1108-1115 |
Abstract | Remote stereocontrol through conformational transmission along a carbon chain is highly important in synthetic systems and molecular architectures. In this work, the interactional reactivity between a remote silicon-based bulky group and an O-/N-containing functional group has been revealed and determined by lateral lithiation–substitution, desilylation, as well as desilylation–olefination with benzaldehyde. The results suggest considerable information transmission and steric hindrance that can be exploited for the controllable synthesis of atropisomeric molecules. Based on the remote steric effect of a functional group across the aromatic ring of an amide, the construction of isolable atropisomeric amides with functional groups, such as alcohol, amine, and olefin was successfully achieved. All these new atropisomers were obtained in reasonable yield in pure diastereomeric form, and the specific configuration of representative products was confirmed by X-ray crystallography. |
Keyword | Lithiation Olefination Organosilicon Remote Control Stereoselective Chemistry |
Subject Area | 物理化学与绿色催化 |
DOI | 10.1002/asia.201301727 |
Funding Organization | the National Natural Science Founder of China (No. 21173064;21133011);Zhejiang Provincial Natural Science Foundation of China (Q12B020037);Program for Excellent Young Teachers in Hangzhou Normal University (HNUEYT, JTAS2011-01-014) |
Indexed By | SCI |
If | 4.587 |
Language | 英语 |
Funding Project | 均相催化课题组 |
compositor | 第一作者单位 |
Citation statistics | |
Document Type | 期刊论文 |
Identifier | http://ir.licp.cn/handle/362003/21229 |
Collection | 羰基合成与选择氧化国家重点实验室(OSSO) |
Corresponding Author | Xia CG(夏春谷); Xu LW(徐利文) |
Affiliation | 1.Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Beijing, Peoples R China 2.Univ Chinese Acad Sci, Beijing, Peoples R China 3.Hangzhou Normal Univ, Minist Educ, Key Lab Organosilicon Chem & Mat Technol, Hangzhou 310012, Zhejiang, Peoples R China |
Recommended Citation GB/T 7714 | Bai XF,Deng, Wen-Hui,Xu, Zheng,et al. Silicon-Based Bulky Group-Induced Remote Control and Conformational Preference in the Synthesis and Application of Isolable Atropisomeric Amides with Secondary Alcohol or Amine Moieties[J]. Chemistry - An Asian Journal,2014,9(4):1108-1115. |
APA | Bai XF.,Deng, Wen-Hui.,Xu, Zheng.,Li FW.,Deng, Yuan.,...&徐利文.(2014).Silicon-Based Bulky Group-Induced Remote Control and Conformational Preference in the Synthesis and Application of Isolable Atropisomeric Amides with Secondary Alcohol or Amine Moieties.Chemistry - An Asian Journal,9(4),1108-1115. |
MLA | Bai XF,et al."Silicon-Based Bulky Group-Induced Remote Control and Conformational Preference in the Synthesis and Application of Isolable Atropisomeric Amides with Secondary Alcohol or Amine Moieties".Chemistry - An Asian Journal 9.4(2014):1108-1115. |
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LZ01029660.pdf(629KB) | 期刊论文 | 作者接受稿 | 开放获取 | CC BY-NC-SA | View Application Full Text |
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