LICP OpenIR  > 羰基合成与选择氧化国家重点实验室(OSSO)
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
DepartmentOSSO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 PublicationChemistry - An Asian Journal
ISSN1861-4728
Volume9Issue: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.

KeywordLithiation Olefination Organosilicon Remote Control Stereoselective Chemistry
Subject Area物理化学与绿色催化
DOI10.1002/asia.201301727
Funding Organizationthe 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 BySCI
If4.587
Language英语
Funding Project均相催化课题组
compositor第一作者单位
Citation statistics
Cited Times:13[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://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 AuthorXia CG(夏春谷); Xu LW(徐利文)
Affiliation1.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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