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.
Stereo- and regioselective opening of 3-phenylglycidates by trifluoromethylsulfonamide under solid-liquid heterogeneous conditions / M. Penso, D. Albanese, D. Landini, V. Lupi. - In: CHEMISTRY LETTERS. - ISSN 0366-7022. - :5(2001), pp. 400-401.
Stereo- and regioselective opening of 3-phenylglycidates by trifluoromethylsulfonamide under solid-liquid heterogeneous conditions
D. AlbaneseSecondo
;D. LandiniPenultimo
;
2001
Abstract
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.
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