Back to Search Start Over

Preparation of Fluoroalkyl Imines, Amines, Enamines, Ketones, α-Amino Carbonyls, and α-Amino Acids from Primary Enamine Phosphonates.

Authors :
Palacios, Francisco
de Retana, Ana Maria Ochoa
Pascual, Sergio
Oyarzabal, Julen
Source :
Journal of Organic Chemistry. 12/10/2004, Vol. 69 Issue 25, p8767-8774. 8p. 6 Diagrams, 6 Charts.
Publication Year :
2004

Abstract

A simple method for preparation of fluoroalkyl β-enaminophosphonates 1 from alkylphosphonates 2 and perfluoroalkyl nitriles 3 is reported. Olefination reaction of functionalized phosphates I with aldehydes gives α,β-unsaturated imines 5. Acid hydrolysis of these fluoroalkyl derivatives 5 affords α,β-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 α-amino aldehydes 12, α-amino ketones 13, or α-amino acid derivatives 14. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00223263
Volume :
69
Issue :
25
Database :
Academic Search Index
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
15618593
Full Text :
https://doi.org/10.1021/jo048682m