Trifluoromethyloxirane

Discovery of Trifluoromethyl Glycol Carbamates as Potent and Selective Covalent Monoacylglycerol Lipase (MAGL) Inhibitors for Treatment of Neuroinflammation

“…The initial synthesis of PMB-protected chiral glycol 27 was achieved by nucleophilic addition of p -methyoxylbenzyl alkoxide to commercially available racemic epoxide 25 followed by chiral chromatography (Scheme ). Alternatively, racemic epoxide 25 can be resolved using a Jacobsen hydrolytic kinetic resolution reaction to give the desired enantioenriched ( R ) epoxide ( 26 ) in >98% ee . Ring opening of chiral epoxide 26 with p -methyoxylbenzyl alcohol affords the desired enantiomer of 27 without the need for chiral chromatography. …”

Ring‐Opening Lithiation–Borylation of 2‐Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

“…In the presence of nucleophiles,i tu ndergoes ring-opening at the less-sterically hindered methylene position to give a-trifluoromethyl secondary alcohols. [8] Stereospecific metalation of the more acidic methine followed by electrophile trapping or cross-coupling and subsequent epoxide-opening leads to a-trifluoromethyl tertiary alcohols. [9] a-Trifluoromethyl boronic esters are potentially valuable intermediates for the preparation of diverse trifluoromethylated products owing to the versatility of the boronic ester, [10,11] which can be stereospecifically transformed into av ariety of functional groups.…”