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    
Abstract/OtherAbstract:
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.
Authors:
Francisco Palacios; Ana María Ochoa de Retana; Sergio Pascual; Julen Oyarzabal
Related Documents :
11383895 - A study of the donor properties of sialyl phosphites having an auxiliary 3-(s)-phenylse...
10822585 - Abbreviated synthesis of the c3-c14 (substituted 1,7-dioxaspiro[5.5]undec-3-ene) system...
16233175 - Concomitant extracellular accumulation of alpha-keto acids and higher alcohols by zygos...
4245 - Physico-chemical and immunological properties of acid alpha-glucosidase from various hu...
3233955 - Contact sensitivity to oak moss.
19002965 - The inhibitory effect of glutamate on the growth of a murine hybridoma is caused by com...
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    
Affiliation:
Departamento de Química Orgánica I, Facultad de Farmacia, Universidad del País Vasco, Apartado 450, 01080 Vitoria, Spain. qoppagaf@vc.ehu.es
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Acetaldehyde / chemical synthesis*
Amines* / chemical synthesis,  chemistry
Amino Acids / chemical synthesis*
Imines / chemical synthesis*
Ketones / chemical synthesis*
Molecular Structure
Phosphonic Acids / chemistry*
Chemical
Reg. No./Substance:
0/Amines; 0/Amino Acids; 0/Imines; 0/Ketones; 0/Phosphonic Acids; 75-07-0/Acetaldehyde

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


Previous Document:  Synthesis of novel Bi-, Tri-, and tetracyclic nucleosides by reaction of a common cyclic enamine der...
Next Document:  Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern.