Document Detail


MedLine Citation:
PMID:  18088145     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A new kind of complex prepared from scandium(III) triflate and l-proline-derived N,N'-dioxides has been developed to catalyze the enantioselective aza-Diels-Alder reaction between 1,3-butadiene (diene 1) and aldimines 2, affording the corresponding 2,5-disubstituted dihydropyridinones in moderate to high yields (up to 92%) with good enantioselectivities (up to 90% ee) at room temperature. A variety of aldimines including aromatic, heteroaromatic, conjugated, and aliphatic imines were found to be suitable substrates. Enantiopure samples (up to 99% ee) were obtained for some products by a single recrystallization. The absolute configuration of the products was determined by X-ray diffraction and CD analysis. On the basis of the investigation of 1H NMR spectra and the positive nonlinear effect, the catalyst structure was carefully discussed.
Authors:
Deju Shang; Junguo Xin; Yanling Liu; Xin Zhou; Xiaohua Liu; Xiaoming Feng
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2007-12-19
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  73     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2008 Jan 
Date Detail:
Created Date:  2008-01-11     Completed Date:  2008-03-24     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  630-7     Citation Subset:  IM    
Affiliation:
Key Laboratory of Green Chemistry & Technology, Sichuan University, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
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MeSH Terms
Descriptor/Qualifier:
Aza Compounds / chemistry
Butadienes / chemistry*
Catalysis
Cyclic N-Oxides / chemistry*
Imines / chemistry*
Ligands
Molecular Structure
Organometallic Compounds / chemical synthesis,  chemistry*
Pyridones / chemical synthesis*,  chemistry
Scandium / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Aza Compounds; 0/Butadienes; 0/Cyclic N-Oxides; 0/Imines; 0/Ligands; 0/Organometallic Compounds; 0/Pyridones; 106-99-0/1,3-butadiene; 7440-20-2/Scandium

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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