Syntheses and Configuration Inversion of Substituted Oxazolines

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The present paper covers the simply and highly stereoselective syntheses of (α-S, 4S)-2-dichloromethyl- 4, 5-dihydro-α- ( 4-nitrophenyl)- 4-oxazolemethanol (4a), (α-S,4S)-2-methyl-4,5-dihydro-α- (4-nitrophenyl)-4-oxazolemethanol (4b), and (α-R, 4R)-2-dichloromethyl-4,5-di-hydro-α- [ (4-methylsulfonyl) phenyl] - 4 -oxazolemethanol (4c) with good yields ( 80 % - 900% ). A configuration inversion product, (1R, 2S)-2-dichloroacetamido-1-(4-nitrophenyl)-1, 3-propane-diol (8), was obtained during our attempting to convert compound 4a into (4S, 5R)-2-(dichloromethyl)-4,5-dihydro-5- (4-nitrophenyl)-4-oxazolemethanol(7).
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