Document Detail


Cyclization via carbolithiation of alpha-amino alkyllithium reagents.
MedLine Citation:
PMID:  18700774     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
Robert J Bahde; Scott D Rychnovsky
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2008-08-14
Journal Detail:
Title:  Organic letters     Volume:  10     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-09-12     Completed Date:  2008-11-13     Revised Date:  2013-06-05    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  4017-20     Citation Subset:  IM    
Affiliation:
Department of Chemistry, 1102 Natural Sciences II, University of California, Irvine, California 92697-2025, USA.
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MeSH Terms
Descriptor/Qualifier:
Amines / chemistry*
Carbon / chemistry*
Cyclization
Indicators and Reagents / chemistry*
Lithium / chemistry*
Oxidation-Reduction
Grant Support
ID/Acronym/Agency:
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:
0/Amines; 0/Indicators and Reagents; 7439-93-2/Lithium; 7440-44-0/Carbon
Comments/Corrections

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