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Beilstein J. Org. Chem. 2011, 7, 246–253, doi:10.3762/bjoc.7.33
Graphical Abstract
Scheme 1: General route to oxazolidinones via a palladium-catalyzed reaction.
Figure 1: Metal–olefin complexation from the anti-face of the double bond.
Figure 2: Cyclic systems with enantiotopic leaving groups at allylic positions.
Scheme 2: The cycloheptatriene–norcaradiene equilibrium.
Scheme 3: Synthesis of oxazolidinone 9 starting from carboxymethyl cycloheptatriene 5a.
Scheme 4: Attempted isomerization of 7 to 10.
Scheme 5: Synthesis of oxazolidinones 17 and 20.
Scheme 6: The mechanism for the formation of oxazolidinones [3].
Figure 3: Nucleophilic attack on the double bond from the leaving group's side.