Chemistry Letters, Vol.30, No.5, 400-401, 2001
Stereo- and regioselective opening of 3-phenylglycidates by trifluoromethylsulfonamide under solid-liquid heterogeneous conditions
Ethyl cis- and trans-3-phenylglycidates have been opened stereo- and regioselectively with trifluoromethylsulfonamide in the presence of catalytic amounts of solid sodium carbonate. Under these conditions, (2R,3R)-3-phenylglycidate produces exclusively ethyl (2R,3S)-3-N(trifluoromethanesulfonyl)amino-2-hydroxy-3-phenylpropionate deriving from the attack of the nucleophile on the C-3 carbon atom.