HEXACHLOROCYCLOPENTADIENE IN DIELS-ALDER ASYMMETRIC REACTION

Date

1994-02-14

Author

AKHMEDOV, IM
PEYNIRCIOGLU, B
MAMEDOV, EG
Tanyeli, Cihangir
DEMIR, AS

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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.

Subject Keywords

Acid, Acrylate, conformations

URI

https://hdl.handle.net/11511/42466

Journal

TETRAHEDRON

DOI

https://doi.org/10.1016/s0040-4020(01)85072-9

Collections

Department of Chemistry, Article

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Citation Formats

I. AKHMEDOV, B. PEYNIRCIOGLU, E. MAMEDOV, C. Tanyeli, and A. DEMIR, “HEXACHLOROCYCLOPENTADIENE IN DIELS-ALDER ASYMMETRIC REACTION,” TETRAHEDRON, pp. 2099–2106, 1994, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/42466.