Synthesis of phosphatidic acids via cobalt(salen) catalyzed epoxide ring-opening with dibenzyl phosphate

Abstract

With a CoIII(salen)OTs catalyst, dibenzyl phosphate ring-opens a variety of terminal epoxides with excellent regio-selectively and yields up-to 85%. The reaction is used in a highly efficient synthesis of enantiopure...

Solvent-Free Tandem Reaction of P(O)–OH and an Epichlorohydrocarbon for Controllable O-Alkylation through a Ring-Opening and Annulation Process

“…20 Because the amounts of the dechlorinated products gradually increased on prolongation of the reaction time or on an increase in the temperature, and because three-and four-membered rings are unstable, the O-alkylation probably proceeds through a tandem reaction involving a ringopening and an intramolecular annulation process. [21][22][23][24][25][26][27] Attempts to react 2-(chloromethyl)-1,3-dioxolane (2d), containing a five-membered ring, or 2-(chloromethyl)tetrahydro-2H-pyran (2e), containing a six-membered ring, with 1a resulted in no ring-opened or dechlorinated products being detected, probably because of the stability of fiveand six-membered rings (Equation 2). This document was downloaded for personal use only.…”

Synergistic Effect of BaCl2 on Corrosion Inhibition of Copper by Mentha Spicata Oil in 1M Nitric Acid: Gravimetric and Raman Spectroscopy Studies

“…[1][2][3][4][5][6][7][8][9] Moreover, epoxides are key materials for fine chemical synthesis due to their ring-opening activity. [10][11][12][13][14][15][16][17][18] Nowadays, the catalytic cycloaddition of CO 2 to different epoxides attracts considerable attentions of researcher all over the world as an efficient way for cyclic carbonates production as well as one of the best possible strategy for carbon dioxide neutralization by its fixation and recycling. [19][20][21][22][23][24][25] Nevertheless, the direct epoxidation of unsaturated compounds with chemical oxidants, e.g., organic hydroperoxides, leads to the formation of undesired by-products and is ineffective in many cases.…”

Concise Synthesis of Glycerophospholipids

“…Phosphorus-containing small molecules are of particular interest in prodrug design due to their improved selectivity and bioavailability . We believe that this strategy would be an effective tool for incorporating phosphate groups along with Minnaard’s methodology . Furthermore, cholic acid ( 7p , a primary bile acid) also engaged in the epoxide opening with good yield despite the presence of multiple hydroxyl groups.…”

“…30 We believe that this strategy would be an effective tool for incorporating phosphate groups along with Minnaard's methodology. 20 Furthermore, cholic acid (7p, a primary bile acid) also engaged in the epoxide opening with good yield despite the presence of multiple hydroxyl groups.…”

“…17−19 Subsequently Minnaard and colleagues used this method to prepare mono-and diacylglycerophosphates from TBS-protected glycidol with subsequent deprotection and phosphorylation (Scheme 1F). 20,21 This strategy offers selective acylation at the sn-1 position. Although Minnaard's report is the first application of Co(salen)-catalyzed epoxide opening in lipid synthesis, to the best of our knowledge, the opening of epoxides that also feature glycidol phosphate diesters or triester is unprecedented.…”