C-phosphorylated imines in synthesis of non-racemic α-fluoroalkylated aminophosphonic acid derivatives

Recent achievements in asymmetric synthesis of α-polyfluoroalkylated aminophosphonic acid derivatives from C-phosphorylated imines are summarized. The synthetic potential of fluoroalkylated iminophosphonates was revealed by their easy diastereoselective functionalization (hydrogenation, proline-cata...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2022-06, Vol.197 (5-6), p.444-450
Main Authors: Rassukana, Yuliya V., Onysko, Petro P.
Format: Article
Language:English
Subjects:
Cycloaddition
diastereoselective synthesis
Diazomethane
fluoroalkyl
Imines
Iminophosphonates
non-racemic polyfluoroalkylated aminophosphonic acids
Optical activity
Stereoselectivity
Synthesis
trifluoromethyl
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Summary:Recent achievements in asymmetric synthesis of α-polyfluoroalkylated aminophosphonic acid derivatives from C-phosphorylated imines are summarized. The synthetic potential of fluoroalkylated iminophosphonates was revealed by their easy diastereoselective functionalization (hydrogenation, proline-catalyzed Mannich reaction with acetone, cycloaddition with diazomethane) to afford optically active compounds bearing biorelevant α-polyfluoroalkylated α-aminophosphonic fragment.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2021.2008930