167171-66-6Relevant articles and documents
An asymmetric route to the 5,6-dihydro-4H-1,3-thiazine skeleton via an asymmetric hetero Diels-Alder reaction
Marchand,Mauger,Guingant,Pradere
, p. 853 - 856 (1995)
Magnesium bromide mediated hetero Diels-Alder cycloaddition of diene 1 (R1 = 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 (R2 = 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.