Intrusion Tolerance Policy Model

Maste

Kinetic Resolution of Morita-Baylis-Hillman Adducts and Aryl Alcohols with a Long Alkyl Chain

MasterThe kinetic resolution of sterically bulky Morita-Baylis-Hillman (MBH) adducts was explored with Lipase TL as a resolution catalyst. The enzymatic kinetic resolution was carried out with a solution containing MBH adduct (0.3 mmol), Lipase TL (100 mg/mmol), vinyl acetate (3.0 equiv.), and sodium carbonate (100 mg/mmol) in toluene (0.5 M) at 25℃. The enzymatic kinetic resolution proceeded with modest enantioselectivity (E = 13-29) to yield the enantio-enriched ester products (95-99% ee) at 57-61% conversion. The kinetic resolution of aryl alcohols with a long alkyl chain was explored as a preliminary study for the synthesis of biaryl symmetric chiral diols. The enzymatic kinetic resolution was carried out with a solution containing the alcohol substrate (0.1 mmol), ionic surfactant-coated lipoprotein lipase (20 mg/mmol), and isopropenyl acetate (1.5 equiv.) in toluene (0.5 M) at 40℃. The enzymatic kinetic resolution proceeded with fine enantioselectivity (E = 63-116) to give esters of good enantiopurities (93-97% ee) at 29-50% conversion