Add time:08/30/2019         Source:sciencedirect.com

Reduction of (4S,5S,6S)-4-hydroxymethyl-5-iodo-6-methyl-1,3-oxazin-2-one 2a and (4S,5S,6R)-4-hydroxymethyl-5-iodo-6-phenyl-1,3-oxazin-2-one 2b with tributyltin hydride in ethanol afforded 1,3-oxazin-2-one 3a and 1,3-oxazolidin-2-one 4b, respectively. Hydrolysis of 3a and 4b under basic conditions led to enantiomerically pure aminodiols 1a and 1b. Reduction of 2b in refluxing toluene led to the unexpected bicyclic tetrahydrofuro[3a,d]-1,3-oxazolidin-2-one 5 as the sole product.

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