Document Detail

Preparation of fluoroalkyl imines, amines, enamines, ketones, alpha-amino carbonyls, and alpha-amino acids from primary enamine phosphonates.
MedLine Citation:
PMID:  15575755     Owner:  NLM     Status:  MEDLINE    
A simple method for preparation of fluoroalkyl beta-enaminophosphonates 1 from alkylphosphonates 2 and perfluoroalkyl nitriles 3 is reported. Olefination reaction of functionalized phosphates 1 with aldehydes gives alpha,beta-unsaturated imines 5. Acid hydrolysis of these fluoroalkyl derivatives 5 affords alpha,beta-unsaturated ketones 6, while their selective reduction with hydrides leads to the formation of allylamines 7, enamines 8, and saturated ketones 9 or amines 10. Selective oxidative cleavage of the carbon-carbon double bond of allylamines 7 gives fluorinated alpha-amino aldehydes 12, alpha-amino ketones 13, or alpha-amino acid derivatives 14.
Francisco Palacios; Ana María Ochoa de Retana; Sergio Pascual; Julen Oyarzabal
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  69     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2004 Dec 
Date Detail:
Created Date:  2004-12-03     Completed Date:  2005-02-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  8767-74     Citation Subset:  IM    
Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain.
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MeSH Terms
Acetaldehyde / chemical synthesis*
Amines* / chemical synthesis,  chemistry
Amino Acids / chemical synthesis*
Imines / chemical synthesis*
Ketones / chemical synthesis*
Molecular Structure
Phosphonic Acids / chemistry*
Reg. No./Substance:
0/Amines; 0/Amino Acids; 0/Imines; 0/Ketones; 0/Phosphonic Acids; 75-07-0/Acetaldehyde

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