Stereodivergent synthesis of sulfoxide-containing oxazolidinone antibiotics

Carbamate 5 was prepared under mild conditions via a novel metal–halogen exchange procedure without competing benzyne formation. Selection of an appropriate oxidation/reduction sequence afforded access to either the cis- or trans-1-oxo-4-aryltetrahydrothiopyran system, important intermediates in the synthesis of a new class of oxazolidinone antibiotics.