1985 Volume 49 Issue 6 Pages 1669-1674
The Stereochemical inversion of (R)-5-hydroxymethyl-3-tert-butyl-2-oxazolidinone (1a) or (R)-5-hydroxymethyl-3-isopropyl-2-oxazohdinone (1b) to the corresponding (S)-isomer was accomplished via a key intermediate, (R)-3-N-ethoxycarbonyl-N-tert-butylamino-1, 2-epoxypropane (5a) or (R)-3-N-ethoxycarbonyl-N-isopropylamino-1, 2-epoxypropane (5b), in a high enantiomeric excess. (S)-1a (99% e.e.) or (S)-1b (97% e.e.) was thus obtained from the respective (R)-isomer (1a; 99% e.e., 1b; 95% e.e.).
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