Document Detail


Cooperative Thiourea-Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN.
MedLine Citation:
PMID:  22011108     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
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.
Authors:
Zhiguo Zhang; Katharina M Lippert; Heike Hausmann; Mike Kotke; Peter Richard Schreiner
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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:  -    
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