Document Detail

The vinylfluoro group as an acetonyl cation equivalent: stereoselective synthesis of 6-substituted 4-hydroxy pipecolic acid derivatives.
MedLine Citation:
PMID:  19968262     Owner:  NLM     Status:  MEDLINE    
An unprecedented cascade of reactions after acid-catalyzed hydrolysis of tert-butyl (2S,5S)-2-tert-butyl-5-(2-fluoroallyl)-3-methyl-4-oxoimidazolidine-1-carboxylate 3a leading to pipecolic acid derivative 5 is presented. The vinylfluoro group is shown to be an acetonyl cation equivalent under acidic conditions. Interestingly, vinylchloro and vinylbromo groups do not show such transformation under the same conditions. The pipecolic acid derivative 5 produced in this way is further used to synthesize (2R,4R,6S)-6-tert-butyl-4-hydroxypiperidine-2-carboxylic acid 9.
Nirupam Purkayastha; Deepak M Shendage; Roland Fr?hlich; G?nter Haufe
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  75     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2009-12-28     Completed Date:  2010-03-12     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  222-5     Citation Subset:  IM    
Organisch-Chemisches Institut, Universit?t M?nster, Corrensstrasse 40, D-48149 M?nster, Germany.
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MeSH Terms
Carboxylic Acids / chemistry*
Cations / chemistry*
Imidazolidines / chemistry*
Molecular Structure
Pipecolic Acids / chemical synthesis*,  chemistry*
Piperidines / chemistry*
Structure-Activity Relationship
Vinyl Compounds / chemistry*
Reg. No./Substance:
0/(2R,4R,6S)-6-tert-butyl-4-hydroxypiperidine-2-carboxylic acid; 0/(2S,5S)-2-tert-butyl-5-(2-fluoroallyl)-3-methyl-4-oxoimidazolidine-1-carboxylate; 0/Carboxylic Acids; 0/Cations; 0/Imidazolidines; 0/Pipecolic Acids; 0/Piperidines; 0/Vinyl Compounds; 14228-16-1/4-hydroxypipecolic acid

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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