Document Detail


Quantitative DFT modeling of the enantiomeric excess for dioxirane-catalyzed epoxidations.
MedLine Citation:
PMID:  19243187     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Herein we report the first fully quantum mechanical study of enantioselectivity for a large data set. We show that transition state modeling at the UB3LYP-DFT/6-31G* level of theory can accurately model enantioselectivity for various dioxirane-catalyzed asymmetric epoxidations. All the synthetically useful high selectivities are successfully "predicted" by this method. Our results hint at the utility of this method to further model other asymmetric reactions and facilitate the discovery process for the experimental organic chemist. Our work suggests the possibility of using computational methods not simply to explain organic phenomena, but also to predict them quantitatively.
Authors:
Severin T Schneebeli; Michelle Lynn Hall; Ronald Breslow; Richard Friesner
Related Documents :
12067507 - "slip and fall" theory--extreme order statistics.
15325897 - Bridging between basic theory and clinical practice.
19622317 - Replicated nil associations of digit ratio (2d:4d) and absolute finger lengths with imp...
18453457 - Agent-based modeling: a new approach for theory building in social psychology.
15103237 - Improved resolution on the phylogenetic relationships among pseudomonas by the combined...
21415177 - Particle capture into the lung made simple?
Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  131     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2009 Mar 
Date Detail:
Created Date:  2009-03-18     Completed Date:  2009-06-12     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  3965-73     Citation Subset:  IM    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Catalysis
Epoxy Compounds / chemistry*
Models, Molecular*
Organic Chemistry Processes
Quantum Theory
Grant Support
ID/Acronym/Agency:
GM 40526/GM/NIGMS NIH HHS; R01 GM040526/GM/NIGMS NIH HHS; R01 GM040526-21/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Epoxy Compounds; 157-26-6/dioxirane
Comments/Corrections

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


Previous Document:  Antioxidant single-walled carbon nanotubes.
Next Document:  Acid-catalyzed oxygen-18 labeling of peptides.