Lewis acid catalyzed diels-alder cycloadditions of chiral butenolides to cyclopentadiene: Endo/exo stereoselectivity.

Zhiyu Chen, Rosa M. Ortuño

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

The influence of several Lewis acids as catalysts in the Diels-Alder cycloadditions of cyclopentadiene to (R)-β-angelica lactone, 1, and (S)-5-hydroxymethyl-2(5H)-furanone, 2, respectively, have been investigated. The best results have been provided by the pair ZnCl2/EtAlCl2 for 1 and by Znl2 for dienophile 2, enhancing significantly the rate and the stereoselectivity of these reactions and affording the corresponding endo adducts in 80-90% yields. © 1994.
Original languageEnglish
Pages (from-to)371-376
JournalTetrahedron: asymmetry
Volume5
Issue number3
DOIs
Publication statusPublished - 1 Jan 1994

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