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HEXACHLOROCYCLOPENTADIENE IN DIELS-ALDER ASYMMETRIC REACTION

1994-02-14
AKHMEDOV, IM
PEYNIRCIOGLU, B
MAMEDOV, EG
Tanyeli, Cihangir
DEMIR, AS
Asymmetric thermal Diels-Alder reactions with chiral dienophiles l-menthyl acrylate and l-menthyl allyl ether, using hexachlorocyclopentadiene (HCC) gave cycloadducts of up to 15%ee. Milder reaction conditions achieved by the use of Lewis acid catalysis increased the optical yields up to 2.8 fold. The catalyzed and uncatalyzed reactions using l-menthyl acrylate result in the formation of adducts having opposite configurations. The products have also been resolved via diastereomer formation as pure enantiomers.