Base induced C-5 epimerisation of 4-methyl-5-phenyl oxazolidinones: Chiral auxiliaries derived from norephedrine and norpseudoephedrine. |
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| Authors: | Stephen G Davies Gilles J -M Doisneau |
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| Institution: | The Dyson Perrins Laboratory, University of Oxford, South Parks Road, Oxford, OX1 3QY, UK |
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| Abstract: | Treatment of cis- and trans-4-methyl-5-phenyl oxazolidinones 2 and 3 with excess butyllithium at 0°C results in C-5 epimerisation, via a common intermediate N,C-5-dianion, generating after protonation a 1:4 mixture of 2:3. |
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