Synthesis and spectral properties of fluorinated α,β-epoxyphosphonates

Unusual ionization of phosphine-boranes under RP-HPLC-HRMS conditions disclose a potential system for reduction of C=O bond

“…[25][26][27][28] Borane complexes used for reduction of aryl alkyl ketones generally provide the appropriate secondary alcohols. [29][30][31][32] In this case, activated phosphine-borane affords alkylarene under very mild reaction conditions. The scope of this transformation is currently underway in our laboratory.…”

Highly Diastereoselective Construction of Carbon– Heteroatom Quaternary Stereogenic Centers in the Synthesis of Analogs of Bioactive Compounds: From Monofluorinated Epoxyalkylphosphonates to α-Fluoro-, β-, or γ-Amino Alcohol Derivatives of Alkylphosphonates

“…for the synthesis of two types of monofluorinated α, βepoxyphosphonates with the vicinal and geminal arrangement of fluorine and phosphorus atoms via a Michaelis-Becker addition or by an intramolecular ring closure reaction (Rapp et al, 2015). Herein, we report our results concerning the diastereoselective synthesis and application of fluorinated epoxyalkylphosphonates toward α-fluoro γ -amino-β-hydroxybutanoic acid (GABOB) as well as β-amino-γ -hydroxyalkylphosphonic acid analogs.…”

“…On the basis of a combination of reactivity and synthetic application of oxiranes in organic synthesis (Parker and Isaacs, 1959 ; Ready and Jacobsen, 2002 ; Azoulay et al, 2005 ; Wu and Xia, 2005 ; Padwaa and Murphree, 2006 ; Fustero et al, 2011 ; Singh et al, 2013 ; Zhao and Weix, 2014 ; Faiz and Zahoor, 2016 ), we decided to apply those three-membered heterocycles toward aminophosphonates. Recently we developed the method for the synthesis of two types of monofluorinated α, β-epoxyphosphonates with the vicinal and geminal arrangement of fluorine and phosphorus atoms via a Michaelis-Becker addition or by an intramolecular ring closure reaction (Rapp et al, 2015 ). Herein, we report our results concerning the diastereoselective synthesis and application of fluorinated epoxyalkylphosphonates toward α-fluoro γ-amino-β-hydroxybutanoic acid (GABOB) as well as β-amino-γ-hydroxyalkylphosphonic acid analogs.…”

Asymmetric Reaction of α-Diazomethylphosphonates with α-Ketoesters To Access Optically Active α-Diazo-β-hydroxyphosphonate Derivatives

“…Thus, access to various fosfomycin derivatives for the evaluation of their biological activity is of great importance. Although a number of methods have been established for the synthesis of α,β-epoxypropylphosphonic acid and its analogues, only a few methods are involved in achieving α-halogenated epoxyphosphonates, in particular, fluorinated epoxyphosphonates, whose biological activity maybe enhanced remarkably after the introduction of the fluorine atom. − …”