| Cobalt-mediated [3 + 2]-annulation reaction of alkenes with alpha,beta-unsaturated ketones and imines. | |
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MedLine Citation:
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PMID: 19639989 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The utility of cobalt dinitrosyl complexes for the [3 + 2] annulation of alkenes with unsaturated enones and ketimines has been demonstrated. Reaction of a series of cobalt dinitrosyl/alkene adducts with conjugate acceptors in the presence of Sc(OTf)(3)/LHMDS formed two new C-C bonds at the carbons alpha to the nitrosyl groups of the substrate, leading to unusual tri- and tetracycles. Retrocycloaddition of these products in the presence of norbornadiene yielded functionalized tetrasubstituted bicyclic olefins. |
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Authors:
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Jennifer M Schomaker; F Dean Toste; Robert G Bergman |
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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. |
Journal Detail:
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Title: Organic letters Volume: 11 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2009 Aug |
Date Detail:
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Created Date: 2009-09-01 Completed Date: 2009-11-16 Revised Date: 2010-09-27 |
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: 3698-700 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of California, Berkeley, California 94720, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkenes
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chemistry* Catalysis Cobalt / chemistry* Cycloparaffins / chemistry* Imines / chemistry* Ketones / chemistry* Molecular Structure Organometallic Compounds / chemical synthesis*, chemistry Stereoisomerism |
| Grant Support | |
ID/Acronym/Agency:
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GM 25459/GM/NIGMS NIH HHS; GM F32GM080059/GM/NIGMS NIH HHS; R01 GM025459-31/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Alkenes; 0/Cycloparaffins; 0/Imines; 0/Ketones; 0/Organometallic Compounds; 7440-48-4/Cobalt |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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