| Towards more chemically robust polymer-supported chiral catalysts: alpha,alpha-diphenyl-L-prolinol based catalysts for the reduction of prochiral ketones with borane. | |
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MedLine Citation:
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PMID: 14527158 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Roger J Kell; Philip Hodge; Peter Snedden; David Watson |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 1 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2003 Sep |
Date Detail:
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Created Date: 2003-10-06 Completed Date: 2003-12-12 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 3238-43 Citation Subset: IM |
Affiliation:
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Department of Chemistry University of Manchester, Oxford Road, Manchester, UK M13 9PL. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Boranes
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chemistry* Catalysis Cross-Linking Reagents / pharmacology Hydrolysis Ketones / chemistry* Models, Chemical Polymers / chemistry* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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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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