| Chiral magnesium BINOL phosphate-catalyzed phosphination of imines: access to enantioenriched α-amino phosphine oxides. | |
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MedLine Citation:
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PMID: 21413695 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A new method to synthesize chiral α-amino phosphine oxides is reported. The reaction combines N-substituted imines and diphenylphosphine oxide and is catalyzed by a chiral magnesium phosphate salt. A wide variety of aliphatic and aromatic aldimines substituted by electron-neutral benzhydryl or dibenzocycloheptene groups were excellent substrates for the addition reaction. The dibenzocycloheptene protected imines afforded improved enantioselectivity in the resulting products. Substituted diphenylphosphine oxide nucleophiles also showed good reactivity. |
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Authors:
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Gajendrasingh K Ingle; Yuxue Liang; Michael G Mormino; Guilong Li; Frank R Fronczek; Jon C Antilla |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. Date: 2011-03-17 |
Journal Detail:
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Title: Organic letters Volume: 13 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2011 Apr |
Date Detail:
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Created Date: 2011-04-11 Completed Date: 2011-06-27 Revised Date: 2012-09-20 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 2054-7 Citation Subset: IM |
Copyright Information:
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© 2011 American Chemical Society |
Affiliation:
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Department of Chemistry, University of South Florida, 4202 East Fowler Avenue, Tampa, Florida 33620, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amines
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chemistry* Catalysis Imines / chemistry* Magnesium / chemistry* Molecular Structure Naphthols / chemistry* Organophosphorus Compounds / chemistry* Oxides / chemistry* Phosphines / chemistry* Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM-082935/GM/NIGMS NIH HHS; R01 GM082935/GM/NIGMS NIH HHS; R01 GM082935-01A1/GM/NIGMS NIH HHS; R01 GM082935-02/GM/NIGMS NIH HHS; R01 GM082935-03/GM/NIGMS NIH HHS; R01 GM082935-04/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Amines; 0/BINOL, naphthol; 0/Imines; 0/Naphthols; 0/Organophosphorus Compounds; 0/Oxides; 0/Phosphines; 7439-95-4/Magnesium; 7803-51-2/phosphine |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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