| Cyclization via carbolithiation of alpha-amino alkyllithium reagents. | |
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MedLine Citation:
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PMID: 18700774 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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We report a new route to tertiary alpha-amino stereocenters by sequential alkylation of alpha-amino nitriles followed by reductive lithiation of the nitrile and cyclization onto an alkene. Reductive lithiation of alpha-amino nitriles using lithium 4,4'-di-tert-butylbiphenylide (LiDBB) and subsequent intramolecular carbolithiation proceeded with modest to high diastereoselectivity to deliver cyclic or spirocyclic ring systems. The stereoselectivity of these intramolecular carbolithiations was examined using density function calculations to evaluate plausible transition state models. |
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Authors:
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Robert J Bahde; Scott D Rychnovsky |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2008-08-14 |
Journal Detail:
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Title: Organic letters Volume: 10 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2008 Sep |
Date Detail:
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Created Date: 2008-09-12 Completed Date: 2008-11-13 Revised Date: 2013-04-12 |
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: 4017-20 Citation Subset: IM |
Affiliation:
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Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amines
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chemistry* Carbon / chemistry* Cyclization Indicators and Reagents / chemistry* Lithium / chemistry* Oxidation-Reduction |
| Grant Support | |
ID/Acronym/Agency:
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GM-65388/GM/NIGMS NIH HHS; R01 GM065338-01/GM/NIGMS NIH HHS; R01 GM065338-02/GM/NIGMS NIH HHS; R01 GM065338-03/GM/NIGMS NIH HHS; R01 GM065338-04/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Amines; 0/Indicators and Reagents; 7439-93-2/Lithium; 7440-44-0/Carbon |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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