Document Detail

Cooperative Thiourea-Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN.
MedLine Citation:
PMID:  22011108     Owner:  NLM     Status:  Publisher    
We report a new thiourea-Brønsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and ee´s up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.
Zhiguo Zhang; Katharina M Lippert; Heike Hausmann; Mike Kotke; Peter Richard Schreiner
Related Documents :
12234618 - Regulation of anandamide tissue levels by n-arachidonylglycine.
21574608 - Unexpected tricovalent binding mode of boronic acids within the active site of a penici...
976898 - The recovery and identification of fluoroacetamide and fluoroacetic acid from tissues.
7484108 - Fatty acid composition of palatal tissue from denture stomatitis patients.
8915098 - 3-(octadecanoylaminomethyl)indole-2-carboxylic acid derivatives and 1-methyl-3-octadeca...
7769968 - Analysis of lipoxygenase kinetics by high-performance liquid chromatography with a poly...
Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-10-19
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  -     ISSN:  1520-6904     ISO Abbreviation:  -     Publication Date:  2011 Oct 
Date Detail:
Created Date:  2011-10-20     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

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

Previous Document:  Evolutionary cost analysis of valsartan initiation among patients with hypertension: a time series a...
Next Document:  Surface Characteristics of Self-polymerized Dopamine Coating Deposited on Hydrophobic Polymer Films.