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Synlett 1992; 1992(9): 755-756
DOI: 10.1055/s-1992-21483
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Efficient Control of the endo/exo-Selectivity in Intermolecular Hetero Diels-Alder Reactions of a New 1-Oxa-1,3-butadiene with Different Lewis Acids1

Lutz F. Tietze* , Christoph Schneider
  • *Institut für Organische Chemie, Universität Göttingen, Tammannstr. 2, D-3400 Göttingen, Germany
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Publication Date:
08 March 2002 (online)

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Intermolecular hetero Diels-Alder reactions of the heterodiene 3 [N-(4-ethoxy-1,2-dioxo-3-butenyl)-1,3-oxazolidin-2-one] with (Z)-1-acetoxy-2-ethoxyethene (4) and 3,4-dihydro-2H-pyran (7) were studied in the presence of several Lewis acids and trimethylsilyl trifluoromethanesulfonate (TMS-OTf). Depending on the Lewis acid used a stereoselective formation of either the endo- or the exo-Diels-Alder product was observed.