Document Detail


Towards more chemically robust polymer-supported chiral catalysts: alpha,alpha-diphenyl-L-prolinol based catalysts for the reduction of prochiral ketones with borane.
MedLine Citation:
PMID:  14527158     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
alpha,alpha-Diphenyl-L-prolinol derivatives with para-bromo substituents in either one or both of the phenyl rings are easily bound to crosslinked polystyrene beads containing phenylboronic acid residues by Suzuki couplings. By using extended reaction periods boronic acid residues that do not take part in the couplings are simply lost by hydrolysis. The polymer-supported (PS) alpha,alpha-diphenyl-L-prolinols were used to catalyse reductions of several prochiral ketones with borane in tetrahydrofuran at 22 degrees C. The expected secondary alcohols were obtained in high chemical yields and ees were generally in the range 79-97%. One PS catalyst was recycled 14 times without loss of stereochemical performance.
Authors:
Roger J Kell; Philip Hodge; Peter Snedden; David Watson
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  1     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2003 Sep 
Date Detail:
Created Date:  2003-10-06     Completed Date:  2003-12-12     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  3238-43     Citation Subset:  IM    
Affiliation:
Department of Chemistry University of Manchester, Oxford Road, Manchester, UK M13 9PL.
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MeSH Terms
Descriptor/Qualifier:
Boranes / chemistry*
Catalysis
Cross-Linking Reagents / pharmacology
Hydrolysis
Ketones / chemistry*
Models, Chemical
Polymers / chemistry*
Stereoisomerism
Chemical
Reg. No./Substance:
0/Boranes; 0/Cross-Linking Reagents; 0/Ketones; 0/Polymers

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


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