Preparation and characterization of α-fluorinated-γ-aminophosphonates

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

“…A standard N−debenzylation protocol was employed to remove the benzyl protecting group. The hydrogenolysis reaction was catalyzed by palladium on carbon (Pd/C), and was carried out in trifluoroethanol (TFE) as a solvent [34,35]. The free amines 13 were converted into stable oxalate salts 14 with quantitative yields.…”

“…The amines 13 were prepared in a similar manner as described in [35]. Fluoride 11 (1 equiv) was dissolved in 5 mL of TFE and then 10% Pd/C (20% v/v) was added.…”

“…The oxalates 14 were prepared in a similar manner as described in [35]. A solution of amine 13 (1 equiv) was dissolved in an-hydrous diethyl ether and was added dropwise to a vigorously stirred solution of oxalic acid (1 equiv) in diethyl ether under an argon atmosphere.…”

Palladium-Catalyzed Isomerization-Coupling Reactions of Allyl Chloride with Amines to Generate Functionalized Phosphorus Derivatives

“…Cytlak reported the preparation of trifluoromethyl γ-aminophosphonates by nucleophilic aziridine ring opening [21]. The compounds could be prepared starting from an α-amino aldehyde via a Horner-Wadsworth-Emmons (HWE) reaction and subsequent conversions [10,22]. Straightforward and easy-to-handle methods to obtain the compounds still remain a challenge to chemists.…”

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

“…For instance, they were prepared by reductive amination of γ-aminophosphonyl ketones using sodium borohydride [41], or by conjugate addition of diethyl methylphosphonite to 2-cyclohexenone followed by Bucherer–Bergs amino acid synthesis [42]. Another synthetic approach for a series of α-fluorinated-γ-aminophosphonates has been reported through a palladium-catalyzed hydrogenation of α-fluorovinylphosphonates [43]. …”