Synthesis of lipid-based unsymmetrical O, O-dialkylphosphites. Issue 18 (29th April 2015)

• Record Type: Journal Article
• Authors: Berchel, Mathieu; Haddad, Jimmy; Le Corre, Stéphanie S.; Haelters, Jean-Pierre; Jaffrès, Paul-Alain
• Is Part Of: Tetrahedron letters. Volume 56:Issue 18(2015)
• Page Start: 2345
• Page End: 2348
• Publication Date: 2015-04-29
• Subjects: O, O-Dialkylphosphites -- H-Phosphonates monoester -- Fatty alcohols -- Coupling reagent; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.03.093
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: An efficient method for the synthesis of unsymmetrical lipid-based O, O -dialkylphosphites is reported. The reaction implies the use of H -phosphonates monoester ammonium salt which is coupled with a fatty alcohol in the presence of an optimized quantity of pivaloyl chloride (Piv-Cl) as coupling reagent. The reaction conditions offer access to a wide panel of unsymmetrical O, O -dialkylphosphites including either non-functionalized lipid derivatives (lauryl, dodecyl tetradecyl, hexadecyl, octadecyl), ramified lipid (phytanyl), unsaturated lipids (oleyl, linoleyl) or ω-functionalized alkyl alcohols (azide, propargyl, alkenyl).