Supercritical carbon dioxide as a reaction medium for enzymatic kinetic resolution of P-chiral hydroxymethanephosphinates

Kinetic resolution of racemic P-chiral hydroxymethanephosphinates via their lipase-promoted acetylation in supercritical carbon dioxide as the reaction medium was for the first time investigated under various conditions. The reactivity and selectivity could be controlled by changing the pressure.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

Methyl hydroxymethanephenylphosphinateC8H11O3PEe = 4%[α]D = −1.1 (c 1.1, CHCl3)Source of chirality: enzymatic kinetic resolution in scCO2Absolute configuration: R

Methyl acetoxymethanephenylphosphinateC10H3O4PEe = 7%[α]D = +3.4 (c 2.2, CHCl3)Source of chirality: enzymatic kinetic resolution in scCO2Absolute configuration: S

Ethyl hydroxymethanephenylphosphinateC9H13O3PEe = 88%[α]D = −13.4 (c 1.9, CHCl3)Source of chirality: enzymatic kinetic resolution in scCO2Absolute configuration: R

Ethyl acetoxymethanephenylphosphinateC11H15O4PEe = 6%[α]D = +2.9 (c 2.4, CHCl3)Source of chirality: enzymatic kinetic resolution in scCO2Absolute configuration: S

i-Propyl hydroxymethanephenylphosphinateC10H15O3PEe = 28%[α]D = −6.2 (c 1.2, CHCl3)Source of chirality: enzymatic kinetic resolution in scCO2Absolute configuration: R

i-Propyl acetoxymethanephenylphosphinateC12H17O4PEe = 27%[α]D = +10.4 (c 2.1, CHCl3)Source of chirality: enzymatic kinetic resolution in scCO2Absolute configuration: S