ICCAS OpenIR
Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis
Hu, Shenshen; Li, Jiuyuan; Xiang, Junfeng; Pan, Jie; Luo, Sanzhong; Cheng, Jin-Pei
2010-05-26
Source PublicationJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
ISSN0002-7863
Volume132Issue:20Pages:7216-7228
AbstractA new approach of asymmetric supramolecular catalysis has been developed by combining the supramolecular recognition of beta-cyclodextrin (beta-CD) and the superior property of a chiral primary amine catalyst. The resulted beta-CD enamine catalysts could effectively promote asymmetric direct aldol reactions with excellent enantioselectivity in an aqueous buffer solution (pH = 4.80). The identified optimal catalyst CD-1 shows interesting characteristics of supramolecular catalysis with selective recognition of aldol acceptors and donors. A detailed mechanistic investigation on such supramolecular catalysis was conducted with the aid of NMR, fluorescence, circular dichroism, and ESI-MS analysis. It is revealed that the reaction is initialized first by binding substrates into the cyclodextrin cavity via a synergistic action of hydrophobic interaction and noncovalent interaction with the CD-1 side chain. A rate-limiting enamine forming step is then involved which is followed by the product-generating C-C bond formation. A subsequent product release from the cavity completes the catalytic cycle. The possible connections between molecular recognition and asymmetric catalysis as well as their relevance to enamine catalysis in both natural enzymes and organocatalysts are discussed based on rational analysis.
DOI10.1021/ja102819g
Indexed BySCI ; IC ; CCR
Language英语
WOS IDWOS:000277999700062
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/69896
Collection中国科学院化学研究所
Corresponding AuthorLuo, Sanzhong
AffiliationChinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing Natl Lab Mol Sci, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Hu, Shenshen,Li, Jiuyuan,Xiang, Junfeng,et al. Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,2010,132(20):7216-7228.
APA Hu, Shenshen,Li, Jiuyuan,Xiang, Junfeng,Pan, Jie,Luo, Sanzhong,&Cheng, Jin-Pei.(2010).Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis.JOURNAL OF THE AMERICAN CHEMICAL SOCIETY,132(20),7216-7228.
MLA Hu, Shenshen,et al."Asymmetric Supramolecular Primary Amine Catalysis in Aqueous Buffer: Connections of Selective Recognition and Asymmetric Catalysis".JOURNAL OF THE AMERICAN CHEMICAL SOCIETY 132.20(2010):7216-7228.
Files in This Item:
There are no files associated with this item.
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[Hu, Shenshen]'s Articles
[Li, Jiuyuan]'s Articles
[Xiang, Junfeng]'s Articles
Baidu academic
Similar articles in Baidu academic
[Hu, Shenshen]'s Articles
[Li, Jiuyuan]'s Articles
[Xiang, Junfeng]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[Hu, Shenshen]'s Articles
[Li, Jiuyuan]'s Articles
[Xiang, Junfeng]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.