| Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis. | |
| | |
MedLine Citation:
|
PMID: 22145621 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenols is described. The combination of an achiral Lewis base and a chiral Brønsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpentenols to form bromomethyltetrahydrofurans. The constitutional site selectivity is highly dependent upon the aromatic substituent and the configuration of the double bond. |
| | |
Authors:
|
Scott E Denmark; Matthew T Burk |
Publication Detail:
|
Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2011-12-06 |
Journal Detail:
|
Title: Organic letters Volume: 14 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2012 Jan |
Date Detail:
|
Created Date: 2012-01-06 Completed Date: 2012-04-17 Revised Date: 2013-05-22 |
Medline Journal Info:
|
Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
|
Languages: eng Pagination: 256-9 Citation Subset: IM |
Copyright Information:
|
© 2011 American Chemical Society |
Affiliation:
|
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. sdenmark@illinois.edu |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Acids
/
chemistry* Bromine Compounds / chemistry* Catalysis Cyclization Ether, Ethyl / chemistry* Lewis Bases / chemistry* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
|
R01 GM085235-02/GM/NIGMS NIH HHS; R01 GM82535/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
|
0/Acids; 0/Bromine Compounds; 0/Lewis Bases; 60-29-7/Ether, Ethyl |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: No evidence of inbreeding avoidance despite demonstrated survival costs in a polygynous rodent.
Next Document: The effect of radiofrequency radiation on DNA and lipid damage in female and male infant rabbits.