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36348940587
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note
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Note that the order of stereochemical descriptors R/S obey different numeration profiles in compounds 1 and 2. In particular, the α carbon occupies position 2 in the former and position 9a in the latter. Abbreviated names, with and without numerical locants, are exemplified below for clarity. {A figure is presented}
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32
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36348962568
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note
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The preparation of trichloromethyloxazolidinones was preferred to tert-butyloxazolidinones because of their greater stability. In the case of proline, the corresponding trichloromethyloxazolidinone is a crystalline solid, while the tert-butyl derivative is highly sensitive to hydrolysis and unstable in air.
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33
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36348981746
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note
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Unreacted (S,S,S)-1 can be isolated, if desired, by washing the silica pad with MeOH.
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36
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36348973626
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note
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Although the relative spatial disposition of substituents at carbon 9a is identical for all three tetrasubstituted compounds 3a-c, the stereochemical descriptors R/S giving the absolute configuration of the carbon centre differ. Thus, the compound with a benzyl substituent (3b) has an S configuration at position 9a due to the different priority of the substituents in comparison with the methyl or allyl derivatives.
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