406951-62-0Relevant articles and documents
Preparation of fluoroalkyl imines, amines, enamines, ketones, α-amino carbonyls, and α-amino acids from primary enamine phosphonates
Palacios, Francisco,Ochoa De Retana, Ana Maria,Pascual, Sergio,Oyarzabal, Julen
, p. 8767 - 8774 (2007/10/03)
A simple method for preparation of fluoroalkyl β-enaminophosphonates 1 from alkylphosphonates 2 and perfluoroalkyl nitriles 3 is reported. Olefination reaction of functionalized phosphates 1 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.
Fluoroalkyl α,β-unsaturated imines. Valuable synthetic intermediates from primary fluorinated enamine phosphonates
Palacios, Francisco,Pascual, Sergio,Oyarzabal, Julen,Ochoa De Retana, Ana M.
, p. 769 - 772 (2007/10/03)
(equation presented) A simple method for the preparation of fluoroalkyl allylamines or α,β-unsaturated ketones by an olefination reaction of primary enamine phosphonates and aldehydes, followed by selective reduction with hydrides or hydrolysis, is reported. Fluorinated β-amino nitriles are also obtained by an olefination reaction of primary enamine phosphonates with aldehydes and subsequent addition of metalated acetonitrile.
