Abstract
Magnesium bromide mediated hetero Diels-Alder cycloaddition of diene 1 (R 1 = Ph) to chiral N-acryloyl-2-oxazolidinone 4b leads to 5b as the sole adduct formed. Chiral auxiliary removal leads to enantiomerically pure 5,6-dihydro-4H-1,3-thiazine 3 (R 2 = Bn). The selectivity of the cycloaddition is reversed under thermal or high pressure activation. The predominant diastereomeric adduct 6b is isolated in pure form after flash chromatography.
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