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

Zhiyu Chen; Rosa M. Ortuño

doi:10.1016/S0957-4166(00)86208-4

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

Zhiyu Chen, Rosa M. Ortuño

Department of Chemistry

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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 language	English
Pages (from-to)	371-376
Journal	Tetrahedron: asymmetry
Volume	5
Issue number	3
DOIs	https://doi.org/10.1016/S0957-4166(00)86208-4
Publication status	Published - 1 Jan 1994

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

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. {\textcopyright} 1994.",

author = "Zhiyu Chen and Ortu{\~n}o, {Rosa M.}",

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T1 - Lewis acid catalyzed diels-alder cycloadditions of chiral butenolides to cyclopentadiene: Endo/exo stereoselectivity.

AU - Chen, Zhiyu

AU - Ortuño, Rosa M.

PY - 1994/1/1

Y1 - 1994/1/1

N2 - 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.

AB - 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.

U2 - 10.1016/S0957-4166(00)86208-4

DO - 10.1016/S0957-4166(00)86208-4

M3 - Article

VL - 5

SP - 371

EP - 376

IS - 3

ER -

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

Abstract

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